Jolie and I went down to the Portland Art Museum for a meeting with the Events Planner last week.

We looked around at rooms that seated 350+ people. We talked about projectors and coat rooms and WiFi and catering—and everything else you could think of related to holding a major event.

“Look,” I said as we walked past a wide corridor. “That looks like a nice place for the bloggers’ lounge.” The corridor in question also contained a large statue of a naked man, but hey, it’s an art museum.

“We don’t allow red wine in this room,” the planner told me as we walked by another room with 500-year-old paintings. “But white wine? As much as you want!”

Normally I’d be taking notes on all these things—we looked at ten different rooms, all with different seating capacities and red wine vs. white wine specifications. But I didn’t take any notes at all, because I was simultaneously thrilled and terrified, caught up in the Big Idea of what this was all about.

“What do you think?” the cheery Events Planner asked as she walked us out.

I looked up at the impressive building, pictured above and over here. “I’ll take it,” I said. “Let’s do it.”

And thus began the planning…

The Unconventional Book Tour kicks off in just eight days, with my goal of meeting every person who reads AONC in the U.S. and Canada. But as much fun as it will be going from Kansas to Nebraska to meet with 63 small groups, I also thought:

What if we could also bring everyone together in one place? That would be even more epic than me going around from city to city.

So that’s what this is about, and I knew that the “one place” had to be Portland (PDX), World Domination HQ and my hometown of choice. We’ve been scouting event spaces for weeks, trying to find the best location to host an amazing group of people. A place like the Marriott isn’t the right fit, but the smaller hotels were, well, too small.

So I made a big financial commitment to rent the Portland Art Museum, and everything that goes with it—A/V, permits from the city, insurance to make sure no one breaks the naked man statue, and so on. As I suspected, renting out the Portland Art Museum for an entire weekend isn’t cheap. I’m taking a big risk in committing ten months in advance, but nothing worth doing is ever easy.

So, friends: here’s the proposal.

Next June, I propose we take over Portland, Oregon with our first annual World Domination Summit, and I’d love for you to be a part of it.

The summit will be a gathering of remarkable people from all over the world. Other authors, bloggers, and interesting people will be speaking from the main stage, a 376-seat theater where we’ll meet for about a third of the time.

The second part of our time will be in small groups, where we talk about travel hacking, microbusinesses, how to do what you love while changing the world, and all kinds of other important topics. (You’ll sign up for the groups you want, and there will also be a voting system to nominate your own group.)

The final third of the time will be all about community. We’re working with the Mayor’s Office to put together tours of Portland. You can visit the city’s famous food carts, check out the vegan tattoo parlor, head back to the theater for a special Charity: Water screening we’re putting together, or whatever you want.

And mostly, you can hang out with people who see the world in the same way. It will be insanely epic, and I’d love for you to be there.

So here’s the second part of the deal.

The summit will have a cost associated with it, but I’m spending my time thinking about how it can be amazing instead of how it can make money. (“Not many people can guarantee awesomeness, but we’re stepping up” as I say in the Unconventional Guides business.)

It will probably cost about $300 a person or so for the whole thing—much cheaper than SXSW, BlogWorld, or any other major conference that doesn’t have a ton of advertisers. We’re also working with hotels to offer a discounted group rate, talking to both hostels in town to completely book them out, and planning to coordinate some kind of couchsurfing option for people who prefer that.

I’m not 100% sure how everything will work yet, but I have a team of advisers here in Portland helping me to make this much more awesome than I could do on my own. And if you come, you’ll be a big part of making it even more awesome.

The goal is to publish the registration site in mid-September—live from the road as I’m touring America. But before then, I wanted you to be the first to know.

Will you save the date, and set aside June 3-5th 2011? I hope you can make it.

###

Last week I headed out for the Sunday morning long run, and my legs decided not to cooperate. After four miles, it was time to pack it in. Bummer—so I tried again a few days ago.

The same thing happened… almost. At mile four I was ready to quit. Through an act of God and the new Josh Ritter album, I managed to pull it out and keep going. At mile six I was feeling great, and as I headed home, I was glad I didn’t quit. Eleven miles for the win!

***

This post is for the entrepreneurs and business-minded ninjas of our community. It’s all about conducting your own business audit—which basically means “looking closely at stuff and making improvements.”

As I transition from active business development to book tour mode, I’ve been taking a close look at how the Unconventional Guides business operates on its own. I want to make sure the store continues to operate well, even without a bunch of big launches and promotions.

I should say first that I’m pretty bad at most optimization or efficiency efforts. I’m just not motivated to revisit things once they’re done. For better or worse, I almost never go back to something I’ve done before. I also believe that it’s better to focus on the future than the past—better to move on and do something new.

This philosophy works… most of the time. But it’s also true that a good business needs nurturing and continuous improvement. I do this for life in general towards the end of the year in the Annual Review series. Now I’m doing a smaller version for my business this summer.

An audit has a few different meanings. In this context, I think of it as: “a thorough review of information.” In my case, I’ve been looking at the following questions in some detail. You may want to answer these yourself, and—even better—take action to create the improvements you identify.

“Where do you make money?”

In any given business, it’s very easy to get trapped into all kinds of things that have nothing to do with making money. The solution to this is simple: focus on the money. True, money isn’t everything, but in a business, the money is pretty important.

In the audit, you’ll want to look at where the money comes from and determine what you can do to keep it coming. Sometimes new opportunities present themselves; sometimes there’s an easy fix you can make to turn on another tap.

Here’s a big hint: if you have a range of projects, products, or activities, it’s almost always better to devote your efforts to the strong performers than to try and pull up the weak ones. Most people do the opposite. If your goal is for everything to be average, that’s the best you’ll ever get.

“How good is your messaging?”

If you do any kind of online marketing, go back to where you started and read the copy (text) carefully. Review each page of the sales material slowly, and then read it out loud. Does it still present the message that you want?

When I started looking through all of my active sales pages and reference material, I found plenty of mistakes. Typos that were missed a year ago were still there on the page. A date I referenced six months ago is now four months in the past. Oh noes!

Then I checked out the multimedia. When I first started making videos, I was terrible at them. One time someone suggested I “do another take” to improve. Little did they know that the published one was Take #11! It really is an acquired skill. I just kept going and putting them out, which is the right approach, but now that I’m better at it, the old ones need to be replaced. I’ve fixed two of them and will redo another couple of them this weekend.

“Are your prices what they should be?”

When was the last time you raised your prices? You can have a sale or give out discount codes from time to time, but like all businesses, you should also plan on raising your prices on a regular basis as well.

The other day on Twitter someone suggested that prices should be “fair to everyone.” Sorry man, but trying to price for everyone is a business death trap. Don’t do it! I aim solidly for the middle of the market by design—no $10 ebooks, but no $2,000 courses either. It works well. Other businesses are set up to compete on either end of the range, and if it works for them, that’s great.

Since entrepreneurs live by the free market system, the way you answer the question of whether your pricing is fair or not is by asking another question: are people buying what you sell? If yes, you’re probably on the right track. If no, you probably have a problem.

“How are you marketing to existing customers?”

One of the best things you can do is reach out to existing customers and find a way to meet more of their needs. Yet despite the fact that most of my customers buy more than one product, I do very little active marketing to them after the sale. Bad move, Chris! I’m fixing it, with improved follow-up messages in my autoresponder campaign and a postcard mailing drive for a third of the customer list.

As part of this examination, you should also carefully check your post-purchase process. What happens after someone buys? Do they get sent to the right place; does everything arrive in their Inbox or physical mailbox as it should? If you sell consulting, do clients know exactly how to set up a time in your schedule? The easier you can make all of these things, the better.

“Are you tracking, monitoring, or testing enough?”

Until recently, I didn’t even have any analytics software installed on UnconventionalGuides.com. Oops—I’ve fixed that. I’m also starting to do some limited advertising, so the tracking will be critical in resolving the age-old advertiser’s dilemma: “Half the money I spend on advertising is wasted; the trouble is I don’t know which half.” Now I’ll know.

The thing about testing is that you just don’t know what’s going to happen until you do it. That’s why you test! A while back I installed an upsell offer where customers could get a $50 gift certificate for only $25 after making a purchase. I thought it was a killer offer, but my customers didn’t think so—it was accepted only one out of twenty times (5%). A good upsell can convert much better than that, so out went the gift certificates offer.

“Where are the big, missing opportunities?”

Earlier this year I recruited a number of affiliate partners for a major Empire Building launch. I remember looking at the sales figures afterward and seeing a few surprises. A couple of people did very well, even with smaller online profiles. When I noticed this, I thought, “It’s a good thing I recruited them!” But then in the ensuing weeks as I processed my daily mail, comments, and Twitter messages, I noticed a number of people that I hadn’t thought of before. If I had asked them to get involved, the launch could have been even better.

Just because you have a big opportunity doesn’t mean you should pursue it. I pass up a lot of things because they aren’t a good fit for my overall strategy. However, it’s good to know what you’re missing, even if you’re deliberately missing it. In my case, I made a list of opportunities I could pursue in my business. Here’s a short version of the list:

• Add a conference call or webinar series on a specific topic every month
• Create “side products” consisting of smaller versions of the main products
• Create an iTunes app with mini-versions of my products
• Schedule another $100 Business Forum with Pam Slim
• Arrange more joint ventures to promote the guides
• Recruit more “high-end” affiliates
• Create a physical version of the EBK
• Carefully introduce the regular sale of products on eBay
• Conduct a “Pay-what-you-will” event for one of the guides
• Conduct a Silent Auction (or a public auction)
• Improve the social media identity of the biz
• Hire a call center to take orders by phone
• Produce a TV commercial for $100 or less (here’s how)

***

As I said, this is a short version of the list. As to how I evaluate which ideas to pursue at any given time, well, that’s a whole other discussion. In general, though, I follow the “maximalist” approach of trying out a bunch of things all at once and seeing what works the best.

A friend of mine told me recently, “If you love something, you have to protect it.” You could say all kinds of things about that brilliant advice—but in this context, it means that I’ve spent a couple of years constructing a business that supports a good way of life, and I need to take the right steps to protect it. That’s why an audit like this helps.

The Unconventional Guides business won’t ever be huge, but it’s grown much more than I expected when I first sold the first “Discount Airfare Guide” two years ago. I regularly take steps like these to protect it, and to ensure it can thrive even as I travel overseas next week or visit all 50 states this fall. I still have a long way to go in making the project everything I’d like it to be, but I think I’m headed in the right direction.

How about you—will you conduct your own audit? What can you improve?

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Image: Robert

Greetings from Cape Verde, everyone. What a crazy trip it’s been. Over the weekend I’ll return to the U.S., visit Pittsburgh for their TedX event, and make it to Chicago for the beginning of Empire Building week.

One week from yesterday (yikes), I’ll launch my biggest business project of the year while riding the Amtrak rails home to Oregon. If you’re new to AONC or just want to catch up, check out these entries:

1. Recruitment of Case Studies
2. Synchronicity and Empire Building
3. Win a Free Copy “Ultimate Comment Edition” Post
4. Contest Results and a Comment on Comments

***

This brings us to today. The EBK is almost finished (I’m doing a few more case study interviews from the road) and ready to launch out into the world. But first I thought I’d ask an important question… how much do you think it should it cost?

Yes, I really do want to know what you think. You can post your opinion here in the comments, and there’s no wrong answer—just say what’s on your mind and we’ll see what everyone has to say. But if you need more information about it, keep reading.

Where We’re Going

The big question when planning “the next step” for any community is to ask, what is the most natural progression? Where are we going, and how does this step fit into the overall mission?

In terms of the business side of things here, almost everything in the Unconventional Guides store is deliberately under-priced compared to the value it provides. We have a 28-day community group for $100 while plenty of other people in this field charge $150+ for one phone call. We have a Frequent Flyer guide that guarantees at least one free plane ticket for just $49. And so on.

This pricing model has served me well, but it has its skeptics. Every time I raise the price of something, it ends up selling more right away. Strange but true. In Austin recently, I was fortunate to receive business advice from all kinds of people I respect and trust. Every single one of them said: “Don’t underprice this thing! An Empire Building Kit shouldn’t be low-budget.”

(The eminent Copyblogger said to me in a roomful of people who all nodded their approval: “We love you, Chris, but you need to charge more for your stuff.”)

The Goal: Build Your Own Empire

First, here’s the goal: to help aspiring emperors build a successful lifestyle business in one year by doing at least one thing every day. I define lifestyle business as a project that produces at least $50,000 a year in net income with few (or zero) employees, doing something you love that other people are thrilled to pay for.

My preference is for online businesses that can be run from anywhere, since that’s what I do, but the case studies include all kinds of people doing all kinds of things.

There are two “killer apps” to this project. The first is the collection of no-holds-barred case studies, and the second is the step-by-step, one-year plan. Emperors will get the case studies right away, and the 365 steps, tips, and reminders in daily emails for an entire year.

A Chicken for Every Pot

I’ll have three options for the EBK—one on the budget side for people just getting started (“Emperor-in-Training”), one for experienced entrepreneurs who want to take their business to the next level (“Alexander the Great”) , and one in the middle that I think will serve most people the best (“Hail Caesar!”). None of them will be extremely expensive, but none will be cheap either.

All three empire-building options include:

• Numerous (10+) case studies in a range of formats—video interviews, audio interviews, transcripts, and PDF compilations
• A detailed overview of the lifestyle business. What it is? What should you know right from the beginning? How can you create your own empire like all of the case studies have done?
• Additional instructional videos (with key lessons included in text form as well) dealing with specific topics or common questions

In each case study, I talk with the other entrepreneurs all about money—remember, these are people who make $50,000+ a year without employees and by doing something that they love. I ask them: “How did you make this happen? What was your best decision and your biggest mistake? What do you wish you had known when you were first getting started?” And so on. The focus of every conversation relates to this question: “How can other people do what you’ve done, in their own way?”

The middle and premium versions each include a number of materials related to product launches, including a 43-step checklist I use every time I produce a launch. The premium version takes the transparency further by providing a detailed breakdown of the entire Unconventional Guides business—exactly how much money comes in for each product, lessons learned from each launch, copies sold, challenges ahead, and so on.

Anyway, you can view a complete list of everything that’s included next week—for now, I just wanted you to have a good overview. And by the way, if it’s out of their price range, no one should feel any pressure whatsoever about buying the EBK. I’m thrilled that I can publish 90% of my work for free (like the 100 articles a year I post here) or for very low cost (like my upcoming print book, which will hit the stands this fall with a retail price of less than $15).

Wrap-Up

This probably isn’t the most strategic pre-launch message—I’m supposed to be telling you how amazing the EBK is and why you should buy it—but I decided it would be better to hear what people think about the pricing issue first. I’ll cover the rest of the pre-launch on Monday, as long as I get some time away from everything that’s going on in Chicago.

By the way, if you think that making money is outrageous and that I’m a bad person for doing so, then you can go ahead and tell me that here too. I know there are some people who feel that way, so let’s get this out of the way so we can all move on.

For everyone else, I’ll look forward to serving you, either through the Empire Building Kit, something else in the store, or (most important of all) through everything related to the non-profit side of AONC.

But First, the Question

After thinking about it for several weeks and getting input from everyone in Austin, I have a fairly good idea what the price of the EBK should be…. but I’d love to know what YOU think. Nothing is set in stone yet, so I’ll pay very close attention to your responses in making the final decision.

Don’t think about it too much, and don’t worry about giving the “right” answer.

How much should the Empire Building Kit cost? Feel free to provide a specific number, a range, or any general input on price and value.

###

Update: Thanks for all the feedback! There is a huge range of views in the comments — it shows what a diverse crowd we have. I’ll be in Chicago tomorrow and getting ready for the launch on Wednesday.

Image: Olivcris

I’m a big fan of Jim Collins’ work, especially the modern day classic Good to Great.

Even if you’re not interested in business, the book is inspiring and practical. Nine years after publication, it’s still kicking ass, and deservedly so.

I recently re-read my favorite passages, and I especially liked the introduction Jim used to convey how much the book meant to him before publication.

***

As I was finishing this manuscript, I went for a run and an odd question popped into my mind: How much would someone have to pay me not to publish Good to Great?

It was an interesting thought experiment, given that I’d just spent the previous five years working on the research project and writing this book. Not there isn’t some number that might entice me to bury it, but by the time I crossed the hundred-million-dollar threshold, it was time to head back down the trail. Even that much couldn’t convince me to abandon the project.

One hundred million dollars! Can you imagine creating something you love so much that you wouldn’t part with it for less than that? Wow.

Aside from making sure I have enough to live responsibly and have my adventures, I don’t focus a lot on money. But I think Jim’s right: most of us have some kind of walk-away price. It’s good to know what it is, because then you know how valuable your work is—even if it’s something you keep to yourself.

I thought about Jim’s question and tried to apply it to my own world. This year I feel confident in saying I wouldn’t take any less than $2 million dollars to walk away. I’d like to think it was more than that, but I’m not 100% sure. Next year, I hope to say that the hypothetical number is $5 or $10 million—we’ll see.

Understand, I’m not trying to get rich—the real-world, business valuation of my work thus far would be less than any of those numbers. The exercise is to think about the perceived valuation; what it would take for you to hide your work and never show it to anyone.

Most of the time, this is a hypothetical exercise. No one’s going to offer me money to stop writing on ChrisGuillebeau.com – it wouldn’t make sense to belong to anyone else, except for all those other people with the same name… which means pretty much no one.

The point is to keep increasing the perceived valuation of your work.

I feel like I’m making at least a $2 million dollar difference in the world now; Jim Collins felt like his contribution was at least $100 million.

I want to keep improving until one day I can say that I wouldn’t take less than $100 million dollars to stop doing what I do. This sounds like an audacious goal—another topic Jim writes about well.

What’s the price for your work? What would it take for you to quit and walk away?

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Image by Circulating

It’s a new month, and time for a new profile. My friend Tsilli Pines recently quit her job to go full-time with the side business she’s been building for the past three years.

Yay! Congratulations to her.

And when we were talking, she told me how she had worked at the job for eight years, and has spent the past three years carefully building her business to the point where she could take a big leap.

Entrepreneurs are often thought of as embracing risk—but I think this is a bit overrated. In Tsilli’s words: “I’m very conservative about making decisions. I probably could have quit the job last year, but I wanted to wait until I was absolutely sure.”

I thought this was fascinating, so I asked her to tell me more. You can read her answers in our interview below.

***

One month ago you left your job of eight years to strike out on your own. How does it feel? 

It feels like freedom!

However, I had a great job working with great people, so leaving was bittersweet. I learned much of what I know and became the designer that I am working with Fine Design Group, and they gave me a lot of room to grow in the years I worked at the studio. 

Then I hit my stride as a designer and started thinking about what I’m meant to do in the long term. I found myself yearning for total authorship. So while the client work I was doing in the studio was challenging and fun, I wondered what I could do if I were my own client.

Tell us a little about your business. What’s a ketubah? Who are your customers, and how do they find out about you?

A ketubah is a Jewish marriage contract. It was traditionally used as a legal document and is now regarded more broadly as a statement of commitment, ritual object, and work of art.

There is a long history of the ketubah being interpreted as an illuminated manuscript, but there aren’t many takes on the form from the perspective of modern design. My clients are design-minded folks who have a hard time finding something that fits with their style but want to include this tradition in their wedding. Most of the pieces I make are for Jewish or interfaith couples (where one person is Jewish and the other is from another tradition), but I’ve also made Quaker wedding certificates, which are similar documents.

Many people find me online—this is a product people search for pretty specifically. Now that I have been doing this for several years, I’m also getting referral business from happy clients. I try to take really good care of people, so it’s the highest compliment when someone recommends me.

How did you build the business on the side while working full-time?

I built the business really slowly and organically and fit it between the cracks. Two years before I launched my website, I met the owner of a Judaica shop in California, who encouraged me to try out my designs through her store. I worked up two prototypes and the day after I dropped them off, I had my first order.

For those first two years, I only had a handful of clients, because it was all I could handle while getting my head around the process. I learned the ropes by putting one foot in front of the next, getting guidance from the Judaica shop and a few rabbis, and making lots of mistakes.

After that initial period of incubation I felt confident that I had the basics under control: how to work with different texts and what the rules were around them, how to make the pieces, how to package and ship them. But I had never worked directly with any clients because I had the shop handling the first steps of the process. It was a wholesale relationship and I wanted to create a direct relationship with my clients.

I requested a chunk of time off from my job—a combination of vacation I had built up and unpaid time—so that I could focus on taking things to the next level. I got a month off and in that time, I developed a few more designs, designed and coded a website, figured out how I would take direct payment, researched ways to improve my process, and started doing PR to get the word out. 

Knowing that people were increasingly looking for their ketubah online, and being a web designer by trade, I focused on how to make myself most visible online. I decided early on that besides having an easy-to-use website that was optimized for search engines, blogs would be the best way to raise awareness about my work. I already followed a lot of design and wedding blogs because I was interested in their content, so I wrote a very simple email introducing myself politely, with a few images of my work. The response was wonderful and I immediately became visible.

Tip from Tsilli: For folks who are looking to market their work online, I highly recommend Grace Bonney’s generous notes about how to approach the press and most especially this round-up from design bloggers about they like to be approached. In fact, the entire Biz Ladies series is a huge help.

Having an online business makes it easier to do on the side. I determined a reasonable process for fulfilling orders, and then I built a minimum turnaround time around that. Having limited time forced me to think about how to do the work most efficiently. I batched my email responses and did the work that could be done in bursts in the evenings and early mornings. The more involved work of actually producing the pieces was done on the weekends when I had entire days to get into the flow.

But I won’t lie: the beginning was insane. I was basically working two jobs, and my husband was helping me build the infrastructure—also on the side, since he has his own day job. He continues to support the project to this day. I couldn’t have done it without him.

It got to the point last year where there weren’t enough hours in the day, and I could only be reactive in fulfilling orders, rather than proactive in my business planning. It was clear that something had to give. But after four years of growing slowly, I finally felt confident that I had a viable business, and that allowed me to leave my day job.

When did you first think about quitting the day job—was it something you planned from the beginning of the startup, or was it after things began to grow? 

I am a very cautious person and entrepreneurship always seemed risky to me. For many years, I focused on finding the best possible job working for other people in order to avoid that perceived risk. I found the perfect job, but after putting in a good chunk of years, I started to wonder what was next for me.

I always knew I wanted to create something of my own and was drawn to the dream of being a working artist rather than a commercial designer. But I didn’t really see how the money side would work. 

As I’ve grown my own practice, I’ve become increasingly entrepreneurial about it, and the small successes have encouraged me to push ahead. I now see the larger picture and realize that there are so many directions I can take things. This was harder to see when I started out. The path has appeared beneath my feet.

Did anything go wrong in the early development of the business? (If so, what did you learn?)

Oh, so many things have gone wrong. Luckily, they have all been fixable. Packages have gone missing, equipment has failed, mistakes have slipped past both me and my clients, all kinds of things! But with determination and a positive attitude, nothing has been insurmountable.

A lot of the learning process about my internal process revolved around the technical side of things—figuring out the best materials, gear, and process. Often revelations and improvements came out of failures. It’s been a constant learning curve. Tools change, materials are discontinued. So the biggest lessons there were:

Stay nimble. Designing a product means that available materials and tools will change. Keep your eye on the prize and know what you’re trying to do overall, rather than getting hung up on exactly how.

Invest in the right tools. Bootstrapping was critical to the early stages of my business. But I also held out longer than I should have on gear that helps me do my work. 

Stay engaged. Keep trying to understand how your clients experience your product and service, and always work on how to solve more for them. Don’t get complacent.

The things that went wrong externally were often related to factors beyond my control, like shipping mishaps. Any problem that came up was mitigated by taking good care of my clients. I used the following principles to guide me through every situation:

Be clear. If a misunderstanding happens and causes a problem, assume it’s because you weren’t clear, understand why it happened, and adjust all future communication. 

Manage expectations. Be very explicit about how you work, and why. Do exactly what you say you’re going to do, or exceed expectations.

Be generous. Once you’ve set up all the basic rules of engagement, there will be times when something goes wrong, anyway. Go above and beyond what you have to do and make people happy.

The most important thing I got right quickly was knowing what kind of business I was in. It allowed me to say yes to the right things and no to the wrong ones. For example, I decided right away that I was not in the custom design business. This was an important decision because my schedule didn’t allow for it. Just knowing that gave me a framework for what kind of work I could do, which set the stage for everything else. I referred people who wanted a custom design to other artists I respected who did do that kind of work.

What is the greatest thing about your new self-employed life?

The freedom to finally work on all the projects I’ve been scribbling about and thinking about for so long. The ability to take care of other aspects of my life besides work because I am no longer working two jobs. The feeling of total control over my time and my future.

What is your advice to someone who wants to “escape” from traditional work and start something like this?

Find what you love to do, and then do it, even if it doesn’t bring in money at first. Experiment on the side, experiment on the cheap. It’s the single most important concept to grasp if you are looking to build something from scratch.

What worries you?

Everything! I’m a chronic worrier. But there’s a bad way to worry, and a good way. 

The bad way of worrying paralyzes you. You worry you won’t make the money side work, and it seems so overwhelming that you decide not to even try. I used to worry in this way, and did nothing.

The good way of worrying keeps you competitive, keeps you striving. For example, I still worry about making the money side work (especially now that I’ve thrown my weight into my own business completely). I still think, “What if all the work dries up? What if a competitor comes into the market that takes away my market share?” But I worry about it differently now. I worry about it by thinking ahead of the curve, recognizing what my strengths are and what I can do to mitigate that risk.

Now that you have more time to devote to the business, what’s next for New Ketubah and you? Do you plan to hire people or stay small? 

I plan to keep things small, but do big work. I’m energized by the idea of scaling talent, in the model Jonathan Fields describes as Simplicity Driven Entrepreneurship.

I have big plans for this breakout year of mine. Some of them have to do with New Ketubah, and some are new art and design projects. Among other things, DIY Ketubah just launched today! I am giving my most popular ketubah texts away for free as a download and inviting people to share the pieces they produce with it. I want to help accelerate the growth and exploration of this centuries-old tradition by enabling more people to make their own pieces and share their projects to inspire the community as a whole.   

My weekly practice is still ongoing. I regularly post pieces that I make on a rolling basis—these include cards for people I care about, free desktop calendars for anyone to download, and my newest project: visual conversations with other artists.

I’ll also begin offering some of my design work for sale as prints, and will be rolling out a new collection of products that I am making to recast the expressions of Jewish identity I grew up with.

And that’s just the first half of the year! There are some super secret things brewing thereafter, and I hope some of the great people from AONC will join me in the journey.

***

Congratulations to Tsilli!

If you like Tsilli’s work, you can join her newsletter here or follow her on Twitter here. You can also post any follow-up questions for her in this post.

And good luck to everyone else out there who is pursuing a dream of your own. I’ll look forward to hearing about your story one day.

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I wrote a feature article for Writer’s Digest this month, and it looks like it just hit the newsstands. I also received permission to include the full PDF here if you’re interested:

Changing the Rules for Unconventional Success

You can also read a brief online supplement on their site here.

***

I’ve thought about producing a guide about freelance writing, but the reality is that it’s really tough to make it as a freelancer these days. Until I find a way to stretch it out (no one wants to buy a one-page information product), here is the Unconventional Guide to Freelance Writing:

1. Don’t do it the old way. You’ll starve!
2. Find a way to take control of the process. You’ll win!

But if you want more than that, here’s 2,000 words on making a living as a writer, free of charge.

It talks about why I write a newspaper column that no one reads, why I’ll syndicate to almost any outlet, and why I don’t care that CNN doesn’t pay me for the articles they post with my byline. More importantly, it offers guidance for new writers, or those who have been unsuccessful using conventional tactics.

I want to be clear that this piece is for writers who are interested in making some kind of income from their work. There’s nothing wrong with writing for any other reason–I write in a private journal every day, and some of my travel writing is entirely non-commercial.

But I also think it’s perfectly reasonable to want to earn a living as a writer, so that is the group I’m trying to help. For those people, the reality is that it is extremely difficult to support yourself as a successful freelancer by doing things the way they have always been done. That’s why you need to change things up and embrace a new model.

From what I can tell, it seems that some people are arguing about whether the new model is “better” or “worse” than the old one. Alas, this discussion is entirely irrelevant. It doesn’t matter if something new is better or worse than something old; what matters is what you need to do to adapt to it.

I believe the phrase that best applies is “It is what it is.”

Therefore, if you want to work as a writer and don’t want to starve, you have to learn a few new tricks. The good news is that if you learn the new tricks, you can actually do quite well. More here.

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Image: SBGuy

Now that the birthday is over, we’re officially heading into Year Three of World Domination.

A few people said they were surprised that everything has happened so quickly. I regularly receive notes that say “I’ve been reading your blog for years.” It feels like several years to me too—but we’ve only just now crossed the second year point.

Last year I wrote an entire manifesto about creating a writing career in less than a year. To learn more about how it all happened, that free manifesto is probably your best bet.

Just to be clear, though, here are a few more notes. Some of them are specific to blogging and the delightfully strange hybrid career I’ve cobbled together, but I’m pretty sure the principles apply in most creative work.

Set a schedule and never miss a post. My own streak is now 336 posts in a row without ever missing a scheduled day. When you have a streak going, it creates its own motivation because you don’t want to screw it up. As I said in 279 Days, this isn’t so much about the readership—most people would forgive me if I missed a day, and many wouldn’t even notice. Instead, it’s about SELF-DISCIPLINE. Simply put, I need to do this to function well. One mistake leads to another, and I want to keep the streak going.

Get up early and stay up late. If Seth Godin creates an online book launch party and wants the posts to go live at 6am EST (3am on the West Coast, where I live), then you set your alarm for 2:45am and make sure everything is working properly. Yes, it’s possible to queue the post in advance, but what if something goes wrong—don’t you want to make sure that everything is exactly right? How will you tell people about it on Twitter and write an Amazon review?

Since I work from anywhere, I usually just tell people to set the time for a meeting and I’ll accommodate it. Later on I can figure out how to make that work. That said, I did tell Seth: next time, let’s start the book party on PST instead of EST.

Write for both men and women. We recently did an analysis with a random sample of 3,000 names on the email list. Of the names that were easily identifiable, the split was 51/49—almost exactly even (the women won by two points). I liked that. Some blogs are naturally a better fit for either men or women, and that’s totally OK. But for me, I feel like I’m doing something right if it doesn’t trend too far in either direction.

Write for all ages. Wyman Crane is one of our most active commentors and he is 72 years old. You’ll see him in the comments because he often says something about teaching an old dog new tricks. Lorraine Wright, another regular, is 65. She has visited 37 countries and recently set a goal to make it to 100 countries.

We also have a big group of high school students who write in with stories of surviving the culture of mediocrity they encounter in the education system every day. “What if my parents aren’t supportive of my dreams?” they sometimes ask.

My Suggestion: first, tell them you’re dropping out of school, changing your gender, and running away to join the circus. Then say, “OK, I won’t do that, but I do have a couple of other ideas.” That usually works.

So the clear answer is, ignore the idea that you are supposed to break people down in groups based on irrelevant information like age or sex. In other words—don’t focus on demographics, focus on who people really are. “Women ages 25-29 with a college degree” may be the kind of group you think about if you are selling energy drinks, but if you’re trying to change the world, don’t discriminate. I’m honored that so many old, young, and in-between people care about what I’m up to.

Make creative work the most important thing you do. Everyone complains about being too busy, but everyone finds a way to do what’s truly important to them. If watching a TV show is important, you’ll find a way to do it. You’ll watch it online, get it through Netflix and catch up on the weekend, whatever. And that’s fine, because we all do what’s important to us—therefore, all you have to do is make your business/blog/project/etc. extremely important.

Build relationships (really). Yes, I know that the phrase building relationships is starting to go the way of other outdated language thanks to people who have misused or exploited it. Such a shame! I’m interested in actually doing it. I answer all email myself, I don’t accept paid consulting offers, and I maintain a regular correspondence with anyone who wants to write in.

In what became a famous-or-infamous practice (depending on who you ask), I wrote a quick personal note to each of the first 10,000 people who joined the email list in 2008 and early 2009. Yes, 10,000 emails! And often many more afterwards, because people would frequently write back and ask, “Is this an autoresponder?” (Answer: nope.)

If you think this practice is trivial or a waste of time, consider the fact that about 70% of the people who join the list will never leave. I think they’re worth a quick “Hi, thanks for reading.”

Whether you want to write 10,000 emails or not, the point is: the little things matter. Do them.

You want to drop keys everywhere you go, and always focus on why anyone else should care about what you do. Pick up the check when you take people to dinner. Help people without expecting anything in return. If you ask for help yourself and the answer is no, go back and say “No problem, and thank you for considering it.” From what I can tell, only about 20% of people do that.

These things are not really that complicated or difficult. If the people you know aren’t used to them, however, that just means you’ll be that much more special around them. Then maybe they’ll start following the same pattern, and then you’ll know you’re really empowering.

Last but Not Least

Let the record show that this a long journey and I haven’t got everything right yet. I have a lot to learn, and this year I find myself being challenged in all kinds of new ways I haven’t experienced before. The only secret, I think, is continuous improvement. Watch and see.

Finally, to be really successful at something usually requires you to work at for a long period of time. Just keep at it. Don’t quit like everyone else does. When one tactic doesn’t work, try something else.

I’m in it for the long-haul. How about you?

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Image: Jeff

It’s no secret I’m a big fan of author and change agent Seth Godin. I’ve been reading his books since my years in West Africa (2002-2006), and he continues to produce excellent work almost every day on his great blog.

I had the chance to speak to Seth’s “Alternative MBA” group last year, and when the invitation came, I rearranged my schedule and dropped everything to fly to New York. (Never pass up a major opportunity for personal growth.)

Today, Seth’s new book, Linchpin: Are you Indispensible?, launches out into the world. Instead of doing the usual media interviews, Seth decided to promote the book exclusively through the blogosphere. Together with his sidekick Ishita, he recruited a bunch of big-name bloggers – and then me – to publish a group of exclusive interviews today.

You can read the other interviews here, you can buy the book here, and if you’d like to ask Seth a question yourself, you can do so in the comments section of this post.

Let’s get started.

• Linchpin begins with the statement, “This time it’s personal.” This seems to be a departure for you. Among other things, you’re writing about love, binge drinking, urinals, and art. What led to this book?

I’m pretty sure I’m not writing about binge drinking. What I am writing about is the ability of each of us, without authority or permission, to do work that matters, to have an impact and to create a place for ourselves in a society that’s brainwashed us into doing something that’s an easily replaced commodity.

A big part of that is acting like an artist. Being personal, making change, communicating a vision.

I wrote this book for every single person who’s frustrated with the status quo and wants to do more and better work.

• “The system is a mess.” Which system? How does our art change that?

The system of factories churning out stuff we can no longer afford to buy, or to store in our houses overstuffed with junk. The system that turns out college grads who are eager to follow instructions, not blaze a path. The system that depends on spam or churn to grow a product or a brand. And the system that treats employees like disposable cogs in a giant machine.

You know what changes this? Humanity. Connection. Caring. Doing work that’s not easy to replicate. That’s what an artist does.

• According to Linchpin, how do I become an artist? (What if I don’t know what I’m really good at?)

You do art when you make change that matters, and do it via a connection with an individual. A great waitress or conductor or politician can make art. So can David, who cleans the tables at Dean and Deluca. Art isn’t the job, it’s the attitude you bring to the job and work you do when you’re there.

• Are we all really geniuses? If so, what do we do to stop choosing stability over genius?

Well, if a genius is someone who solves a problem in a new and original way, then sure, you’re a genius. And the first step to making that choice is to know it’s available.

• I liked the example of Thomas Hawk putting so much of his work in the Creative Commons. I know that you publish most of your writing for free, too, but what do you do when you run into issues of plagiarism or people otherwise directly stealing from you?

I ask them to stop, or to give readers a link so they can see where it comes from. Of course, if they’re selling it, that’s a different kind of theft, and I ask them them to stop, because then not only am I being ripped off, but so is the buyer.

• “Art is a personal act of courage, something one human does that creates change in another” and “Art is a gift that changes the recipient.” — Would you say that if someone has a talent they keep to themselves, never sharing it with anyone, that they aren’t really making art?

That’s exactly right. According to my definition, doing private stuff doesn’t count… unless, and perhaps, you’re changing yourself.

• Can you tell us more about emotional labor?

Physical labor is digging a ditch. You don’t do it cause it’s fun, you do it because it’s your job. I don’t care if you’re in the mood for it.

Emotional labor is smiling or engaging with someone or bringing insight to your job. Sometimes you do it for fun, but you always do it because it’s your job. I don’t care if you’re in the mood for it.

• “The second person to install a urinal wasn’t an artist, he was a plumber.” Aren’t most of us, in some fashion, plumbers building off each other’s work?

  [A personal example: I read your books while I was in Africa. Now I'm getting ready for my own book launch. Editing the manuscript in December, I could see some artistry and some plumbing, building on the influence of you and other thought leaders. Am I an artist or a plumber?]

I think we surely build on each other. BUT, plumbers don’t really. They don’t strive for a better toilet install, or one that changes the recipient. They strive for a cheap, fast version of the standard and then they move on. Artists take it farther than that, much farther. That’s our assignment.

***

Wrap-Up

I wish Seth well with the launch of Linchpin. It’s a book that deserves wide attention — I received a free review copy, but I also paid full price for an additional copy that’s being sent out from Amazon today.

My work is better because of Seth’s influence and your readership. I’m grateful for both.

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You can join AONC on Facebook here

Today is the launch of my first business project of 2010 and first community group ever.

It’s called the $100 Business Forum, and it’s all about helping 150 people start small businesses on a small budget.

–>Click here to sign up or learn more

***

The premise is that you don’t need a lot of money—or a lot of advance preparation—to start what I call a “very small business.” Really, you don’t need much of anything other than a product or service, a group of people willing to pay for it, and a way for them to pay you. All of that can be done for less than $1,000 in most cases, and less than $100 in many cases.

How It Works

The $100 Business Forum is not a product you buy once and then download. It’s a community group where we’ll all meet every day for 28 days. The group is online, and you don’t have to worry about time zones – you just show up at least once a day for about twenty minutes.

This project is jointly produced with Pamela Slim, author of Escape from Cubicle Nation. Pam and I will co-facilitate the course, but much of the content will come from the participants themselves.

We’ve scheduled two classes so far – the inaugural one starts on February 1 and runs through Feb 28. The second one stars April 5 and runs through May 4.

Because the group will be interacting with each other on a regular basis, we’re limiting each class size to 150 participants. Naturally, since the group is called the $100 Business Forum, the cost is just $100.

–>Read more and sign up here

***

Also, if you’d help us spread the word about this project, I’d really appreciate it. You can direct people to this post or the registration site at 100bizforum.com.

Update: Both groups are sold out! Thanks for your support.

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As part of my Annual Review series, I’m looking back at the development of AONC and the related business during 2009. I hope you’re having a great December, wherever you are.

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The business side of AONC happened quite organically in the beginning. The only real business goal I had when starting the site was to get a book contract. As the readership quickly grew, however, I realized I could also create products to serve specific sub-sets of readers.

Thus was born the Unconventional Guide business, which you can read more about here if you haven’t already seen it. The business vision, in short, is to help people live unconventional lives by creating opportunities through self-employment and travel, while providing me with a sustainable income so I can focus most of my work time on the writing I do for free.

Starting from the ground up in 2008, it took about nine months to put together a model that generated the average annual income for my part of the world ($47,500) while continuing to focus primarily on my writing career. It probably could have been faster, but in the first few months I didn’t even think about the monetization aspect, and then I continued to take the business development side very slowly for the next few months to make sure I was on the right track.

The business grew quite a bit this year from last year’s projections, but it also happened in a very natural way. Since the launch of the first guide (Summer 2008) until now, I’ve consistently spent an average of less than ten hours a week on the business.

This is by design: I enjoy the work, but I also don’t want to become a slave to it. To be fair, much of the other work I do for my writing career (40+ hours a week) influences the success of the business by bringing in new readers, some of whom become customers – but in the categories of business development, content creation, customer support, and other traditional business tasks, I average less than ten hours a week.

Like everything I do, it’s been a work in progress, and I continue to learn as I go along. Speaking of learning, here are a few business lessons learned from 2009.

You don’t have to hire anyone, even as your business grows. After things picked up earlier this year, I felt an internal pressure to hire some kind of virtual assistant, mostly because that’s what everyone in the internet world seems to advise these days. “Get someone to do the things you don’t want to do,” is how the idea is usually sold.

I felt the internal pressure until I realized that another answer to dealing with “the things you don’t want to do” is to just not worry about doing them at all. If I have to supervise someone else doing boring work, it’s not that different from doing it to begin with. The things are still on my mind one way or another.

Instead of expanding the business to the point where I need some form of employees, therefore, I try to keep things very simple. As a reference point, I like this article about Jim Collins, the business author and speaker. Jim has a couple of employees, but the Good to Great empire is deliberately small — so I figure if he can do that at the multi-million dollar level where clients are paying $80,000 a day, I can do just fine at a lower level on my own.

Technically, I’m not entirely on my own. I’m fortunate to work with superstar designer Reese, whom I talk with almost every day. I also have other partners for specific projects, and from time to time someone will help out with a task I couldn’t easily complete by myself. But otherwise, it’s a one-man shop, and I like it that way. If it’s working out OK, why change?

Don’t launch a product the day before leaving the country. Sounds simple, right? But for me it’s hard because I have so many trips planned. I did this with the Social Web launch and it was stressful, even for someone like me who likes to do a lot of things at once. Something always goes wrong with product launches – always – so having at least a day or two of leeway in case of emergency is helpful.

I hope I’ll be able to maintain a good launch + travel calendar in 2010, but with everything going on I’m honestly not sure it will always work out to be at home every time I do something new. Perhaps I should put this on a “Lessons I Should Learn” list.

With coaching and consulting, I like helping people for free more than being paid for it. I know a few other people who are very good at paid coaching – I think of Pam Slim or Charlie Gilkey to start with – and I do understand the psychology behind the fact that you tend to appreciate something more when you pay for it.

But that’s not the way that works best for me. I launched a brief consulting service late last year and had plenty of customer interest, but I felt that the dynamic of the relationship changed when someone was paying me for my time. I shut it down after a few months and no longer accept offers to pay for access.

Never promote anything that isn’t a perfect fit for the community. Thankfully, I didn’t learn this lesson by screwing up somewhere; I just learned to say no more and more often. Every single day I hear from multiple people who all have a new project they’ve worked hard on. In fact, over the course of an average month I’ll hear about 150+ projects that people want me to endorse or promote. “It’s so great!” they tell me. “Your readers will love it!”

And of course, they may be right — but it’s definitely not in the interest of my community to promote 150 things in a month, no matter how great they are. Especially when it comes to paid products, I’m very careful. As I continually remind myself, trust is hard to acquire but easy to lose.

Also, I don’t think there’s anything wrong with promoting things as an affiliate (I have my own affiliate program for the guides), but I’ve learned in my case that it’s usually better to endorse something without receiving anything but goodwill. I’ve done that with Mondo Beyondo, Tribal Author, Escape from Cubicle Nation, and a few books from authors I know.

I’d much rather hear good feedback and strengthen relationships than receive a commission. For me, endorsing stuff is like consulting – being paid just changes the whole dynamic for me, so I prefer to do it without the payoff most of the time.

Make sure each product is accessible and gets potential buyers excited. Commercially speaking, the least successful new product I put out this year was Travel Ninja. In retrospect I realized that some people felt intimidated by it – they could relate to taking a couple of trips or maybe planning for one big adventure, but the idea of traveling as much as I do is certainly not for everyone.

The most successful, on the other hand, was Art and Money (from May-August) and then Frequent Flyer Master (November-December). With FFM, I wanted to make sure I created something that was accessible to people who don’t fly that often. The night before the launch, I still wasn’t sure if I had make the connection strong enough in the landing page and earlier messages.

Thankfully, my confidence grew by mid-morning as we sold out of all 150 introductory copies right away, and then kept going. Lesson learned: make it accessible. Oh, and making it fun helps too.

***

2010 Business Plans

In the first half of next year, I’ll be launching two online communities and one major information product that should ramp up the business profile quite a bit without infringing on everything else we do at AONC.

I’m really excited about all three of these projects. The online communities will provide the chance for a core group of readers/customers to focus on two areas (life planning and entrepreneurship) that are difficult to do in a participatory manner on the blog. Each community will run as a 28-day class where a partner and I do about half of the teaching, and the rest of the input comes from the participants. I’ll be promoting the first one right after New Year’s, and the second one in early March.

The other project will be called Empire Building Kit, and the theme is “How to Build a Business in 1 Year by Doing 1 Thing Every Day.” It’s kind of like the Working for Yourself guide on steroids — or at least, that’s how I’m thinking of it as I’m outlining the content off and on this month.

In the second half of the year, I don’t expect to do much business expansion at all. Instead, the majority of my focus will be on promoting the AONC book and traveling to meet readers throughout the U.S. and Canada. I’ll say more about that in the final Annual Review update, coming next week.

That’s My Story — How About You?

Fellow entrepreneurs – how was your 2009? Any big plans for next year?

And for all of you aspiring entrepreneurs out there – what are you planning to do in 2010 to get closer to your goals?

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