First of all, thanks so much to everyone who signed up to come out the Unconventional Book Tour this fall. My goal was to put this out there and see how people responded.

Well, respond you did! 450 people signed up in the first few hours, and hundreds more over the weekend.

All 63 cities across North America are now represented. NYC, San Fran, L.A., and Vancouver have been fighting it out for the most signups thus far, but people will be out in full force almost everywhere. If you use Twitter, you can search for hashtag #ubt and see some of the other readers who are coming to various cities.

My investment tip for the year is: buy stock in cupcake companies! Business will be good this fall.

A big debate about city choices also broke out in my Inbox, with numerous arguments about whether Oklahoma City is better than Tulsa, why I’m not also going to Canada’s three arctic territories (hint: I’m already going to every state and every province! one thing at a time), and so on.

Thanks as well for your online pre-orders, which helped take the AONC book to the Top 1k on Amazon two months in advance of release. We are also working with local bookstores all across both countries to ensure they know about the book as well, and I certainly encourage you to support your own if you have one. I’ll have much more to say about this whole four-month process later.

***

For now, let’s talk about solutions to problems. If you’re trying to figure out a good idea for a small business, start by looking at a problem that you can provide the solution to. I thought about this last week when I sat down with Charlie Gilkey, longtime friend, new Portland resident, and my business partner on the upcoming Unconventional Guide to Freelancing.

“What’s the number one thing you want people to know about freelancing?” I asked Charlie.

“It’s simple,” he said. “Whether through this guide or something else, the most important thing is that freelancers should view themselves as solution providers instead of just service providers.”

The difference is crucial. If you’re in business for yourself or want to be, you need to think about what kind of solution you’re offering. If you’re solving a problem or relieving a pain, that’s a good start. If you’re just “doing stuff,” you may need to adjust.

The Freelancing Project

If you’re new here, the first half of 2010 has been accelerated, even by my “why not do everything” standard. Last fall I said that 2010 would be the year of scale and reach, which has certainly held true. We’ve built out the business to a more sustainable level, with the flagship Empire Building Kit and upgraded affiliate program. Site readership has nearly doubled from December, along with almost all of the other metrics I track.

As promised several times, after this launch I’ll be retiring from active business development for the rest of the year. The store will still be open, and I’ll still post Sunday Store Updates at least a couple of times a month with news about existing products, but my focus will be on the book tour, Ethiopia project, and the writing I do every day.

Anyway, enough preamble. Here’s the deal: the Unconventional Guide to Freelancing is a one-stop, “Freelancer’s 301” guide to running a service-based business. Our ideal customer for this guide is someone who knows how to do their craft but struggles with running the business.

Important: Charlie and I don’t know how to tell someone to be a web designer, a bookkeeper, a consultant, an agent, or any number or other kinds of specific professions. There are plenty of resources in any one industry to cover that.

But we do know how to condense a wealth of knowledge into a package that freelancers of all kinds can benefit from. That’s what the guide is all about.

In April I went to a higher-price point for the Empire Building Kit because it made sense for that project. (An Empire Building project shouldn’t be super cheap.) For this guide, I’m returning to the lower price point that we’ve used for a few of the earlier guides. I’m happy to do this so the price won’t be an obstacle for anyone who fits the target market.

The launch will kick off on Wednesday morning at 9am PST / 12pm EST. This will be a long-lasting launch, meaning that the guide won’t go away after 24 hours or a week; it will continue to be available in the store on a long-term basis. However, to encourage early participation, Charlie talked me into doing a special Q&A call with the first 150 buyers who pick up the guide on Wednesday.

I make an average of one phone call a day and listen to my voicemail about once a month, so I’m not a big conference call guy. But I agree it will be important to help people who are especially excited about their freelancing biz, so I blocked off an afternoon next month for the call to respond to questions and share a few ideas from the many people we talked with while producing the guide.

(After the Q&A call fills up, we’ll remove notice of it from the launch post—that way, you can tell whether it’s still available or not.)

Thanks!

If the guide sounds like a good fit for you, I’ll look forward to serving you with it on Wednesday. If not, that’s totally fine and I appreciate your time and attention.

By the way… I still can’t believe that so many of you are coming out to visit during the Unconventional Book Tour this fall! It’s going to be epic.

###

Image: Llam

I’ve heard the question in various forms over the past couple of years: Why not just travel around the world without trying to go everywhere—in other words, why focus on the numbers?

My answer is that the numbers give you a goal—something to keep in mind as you go through a challenging process. The numbers can’t be your sole motivation or identity, but they can be a big help.

Pursuing something meaningful and keeping track of it with numbers is fun and addicting. The numbers help to keep things in context. In my business I have goals based on numbers (sales per day, for example). For the blog I have goals based on numbers (new readers joining every day, for example). I don’t do the work for the sake of the numbers, but the numbers provide a good benchmark.

***

Numbers also make the project more interesting to others. In my case, no one would care if I wanted to visit “as many countries as possible.” Come on. We need a goalpost! 192 is the goalpost—not just “a bunch of countries,” but all of them.

Thomas Hawk has a goal of publishing one million processed photos. Nearly all of them are released to the world under a Creative Commons license, and they’re all good photos too. Why one million? Because it’s an audacious number, which makes it compelling to Thomas and interesting for those of us who are following along.

Sean Aiken worked one job a week for 52 weeks across Canada. Isn’t that interesting? I think so. What if he worked five jobs in a year instead of fifty-two? I’d think: good for him, but not as interesting for the rest of us. When you hear “one job a week for a year,” the story becomes much more engaging.

When times are hard, a goal based on numbers also helps you keep perspective. Is it really worth it to go to random places like Equatorial Guinea? For most people, probably not. But for me, yes—because how could I be satisfied with visiting only 100+ countries?

“Well, that was fun—no need to see the rest!”

I don’t think so. What’s a quest without a challenging objective?

Numbers aren’t everything. But under the right conditions and aligned to to the right vision, they can be a lot of fun. My current number is: 143 down, 49 to go.

And how about you—what do you think about numbers?

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Image: Fragmented

I don’t claim to be an expert, but I’ve been writing 1,000 words a day almost every day for the past 120 weeks. That’s the most important tip of all—to be a writer, start writing. You’ll figure out a lot of things along the way.

But for all of you overachievers out there, here are some other ideas that may help.

Move from the general to the specific. Here’s the idea, now here is how you apply it. Give people the concept and then tell them more about how they can use it. Travel is fun and meaningful; here’s how you can actually book a Round-the-World plane ticket. To stand out in life you have to be awesome; here’s what that looks like. Change the world by doing a, b, and c.

Get personal. This is the Penelope Trunk model: often imitated, but seldom to the level of the art form she’s made it. A lot of people copy Penelope’s tactics without relating them to a broader strategy. You have to have a strategy. She does it right; her imitators do it wrong.

Write for an audience of several. I think of about five people when I write. They’re all different, but I try to picture them and think, what would so-and-so think of this? Would he get it? Would she find it interesting?

If it “goes without saying,” you don’t need to say it. I hate reading that phrase… and when I discover it in my work, I hate it even more. Other overused writing phrases include: the jury’s out, think outside the box, it is what it is, and my two cents. Alas, I use them all once in a while.

Always answer the reason why. Why should someone care about what you have to say? Of course your friends and your parents care about what you think, but what about everyone else? You need a clear reason for the rest of the world to care.

Do the second edit later. It’s impossible (well, for me) to write and edit anything longer than an email without needing at least a short break. The longer the draft, the more of a break I need.

Print your work and proof it on paper. I used to write in longhand and transfer it to the laptop, which also helped. Now that I do this for several hours a day, every day, I write almost exclusively on the laptop.

Read everything aloud. There’s something about hearing your work aloud that causes you to notice things you miss when you read. On our annual review trip last December, Jolie read the entire AONC book manuscript out loud over the course of a week (1-2 chapters a day). I couldn’t believe how many mistakes and poor word choices we found! Keep in mind this was after I had been writing the book for six months, and after two complete edits. It was depressing… but hopefully now it’s better because we did it.

Get into the details! Don’t be vague. Provide more info, work it out, tell the whole story. This makes a huge difference. This is why J.D. Roth is such a role model to me. He always tells the whole story. The Yarn Harlot also does this well.

Take the time to do it right. Ramit told me about how he spends 12 hours writing a guest post for someone. Some people are surprised, but that’s how long it often takes! When I get an opportunity to write for a great outlet, whether online or offline, I spend a similarly long time on it.

Preempt objections. This is an important marketing strategy, but it’s also important in your writing. Build your case. If you’re trying to present a viewpoint, think about what the objections will be, then try to preempt them by addressing them (and often negating them) in your writing.

Take a stand. Contrary to conventional wisdom, readers want to know what you actually think. If consensus is overrated, so is neutrality. What bothers you, and what are you doing about it? Tell us.

These books are good: Art and Fear, The War of Art, On Writing, Bird by Bird, and The Elements of Style. But remember, if you want to write, it’s more important to just start writing.

***

Lastly, recognize that any creative act worth doing benefits from an ongoing process of continuous improvement. Writing is no exception. I don’t like everything I wrote in the first two years of the archives here. Next year I probably won’t like everything from 2010. I want my second book to be better than my first, and so on.

That’s just how it goes, and you can’t improve without getting something out there to start with. That’s why the first writing tip is the best: if you want to write, start right now and don’t stop.

What would you add to this list?

###

Image: Phil

I recently met with a guy who’s trying to become a motivational speaker. He’s a good guy with good things to say.

But the thing is… how should I put it… the whole motivational speaker branding doesn’t give a good first impression. It’s old-school at the best of times, and just plain awkward the rest of the time.

And yet, we all enjoy motivation and inspiration. I read Runner’s World every month not because I need any help running (nothing much changes in the world of running from month to month) but because of the inspiring profiles they print. You’ve got the woman who lost 300 pounds by jogging three times a week, the blind guy who ran a marathon with his son, and so on. I’m a sucker for an inspiring story.

So motivation is good—it’s just the branding of motivation that’s awkward. What’s to be done? My friend Colleen, AKA The Great Communicatrix, explained it best one day while we were hanging out in Austin a while back:

You can’t just BE A MOTIVATIONAL SPEAKER. No one likes that shit. What you should do is BE PASSIONATE ABOUT SOMETHING. Show up and talk about something you give a damn about. Your passion will be motivational in itself.

I think Colleen’s right. If you want to be a speaker, you can go to Toastmasters meetings and learn how you are supposed to hold your hands, the right way to make eye contact with the audience, and so on. But I think it’s better to live an active life and figure out what you’re really passionate about. Then, talk about that.

You’ll get better as you go along. If you give a talk and forget something, if you say um or you know too much, if you break some kind of “rule” of speaking protocol, people will get over it.

It doesn’t mean that you shouldn’t try to improve on the technical things. It just means that the message is more important than the presentation. Between passion and presentation, passion wins every time.

“Motivational speakers” try to manufacture motivation, and this doesn’t usually work. Colleen’s way (the better way) is to introduce your passion to the world around you instead. The right kind of passion is both infectious and contagious. Motivation made easy!

How do you want to change the world? Why not take that thing with you everywhere you go?

Get that right first. Then, even if you’re only talking to one person, you just might be a motivational speaker.

###

Image: Adam

Back home in Portland, I went to my first yoga class in several weeks and immediately noticed that something was different.

This class is kicking my ass! I thought—but then I looked around, and everyone else was doing just fine. The same thing happened during my 40-minute run the night before: 20 minutes in, I was ready to give up.

My most recent epic journey was fairly intense. Among other challenges, I slept in a different bed every night for 10 nights in a row. I hadn’t planned it that way—I was in Cyprus for three nights, but I changed rooms one night and hotels the other night. Because of the complex itinerary, I had a lot of transit stops—one night in Munich, one in Miami, one in Heathrow, and so on. Living out of a suitcase can work for a while, but it does wear you down over time.

Flying home to the States from Germany, I was preparing for two big projects—speaking at Carnegie Mellon in Pittsburgh, then launching the Empire Building Kit on board the Empire Builder westbound train from Chicago. I had started working on each of them two weeks before, but Parkinson’s law of “work expands to fill the time allotted to it” kicked in. The night before the talk, I was still shuffling the slides around. Then a few days later on the morning of the launch, I was up at 5:30 a.m. in North Dakota trying to update all the site files before going live.

The two big projects, the hopping around Europe with a bonus trip to Cape Verde, the 46 hours on Amtrak, and everything else contributed to my feeling pretty worn down by the time Portland’s Union Station came into sight. On Thursday I said I was ready for a five-hour nap, but I probably could have used about 50 hours.

Don’t get me wrong—the trip was 100% worth it. I wouldn’t have done it any differently.

I’ve come to believe more and more that saying yes is better than no, an active life is better than a passive one, and embracing adventures are all important aspects of what make many of us happy. If you’re out there doing fun stuff, you can usually ignore people who tell you to “slow down and take it easy.”

Nevertheless, I do get tired doing these things, and I also believe it’s important to rest and recover. Here’s how I do it.

Sabbath Day

I go around the world at least four or five times a year, but home in Portland, I’m kind of a homebody. I don’t go out much, and when I do, I don’t go far. Not owning a car confines me to a 15-block walking radius and wherever the bus or bike will take me, but that’s perfectly fine. I live right in the middle of the city for a good reason.

I generally work six days a week, but on Saturday or Sunday I take most of the day off as a Sabbath day. There are different ways to observe the Sabbath, and I tend to believe that the principle is more important than the “rules” (which is kind of what I believe about everything). The principle is that our bodies and minds need rest, so we should plan a regular winding-down period to ensure we have the strength to keep going.

When I’m traveling, I don’t worry about a day of rest. Sometimes rest just isn’t possible on the road, and other times it will happen naturally at one of the stops. At home, though, I usually take a modified Sabbath from Saturday evening to late Sunday afternoon. During this time I don’t use the computer for much of anything, and it’s the only time during the week when I don’t check email at all.

(I know that other people advocate spending even more time away from the computer, but that doesn’t work for me. I also don’t find that being online all the time is especially draining or disheartening.)

Recovery versus Rest

While rest may be a passive activity—for me it’s reading books and hanging out in coffee shops—recovery is both passive and active. Recovery activities consist of things that help us recharge and get ready for the next thing.

In my case, I go for a long run every week, usually on Sundays. I also review my lists of projects and tasks at least once a week, usually on Friday or Saturday night. I ask: Am I on track? Does something need to change? Am I forgetting something?

This weekend I realized that I haven’t been writing as much as I would like over the past few weeks. It’s a natural consequence of the big launch and all the travel, but I don’t want to lose the habit. Getting back to the writing is a recovery activity. I opened up the files for a couple of big writing projects and immediately felt better. “This is why I do what I do,” I said to myself. “I need to recover so I can do more of it.”

My favorite book about this concept is The Power of Full Engagement, which is a a great response to more traditional “time management” books. I’ve always been skeptical of the idea of managing time—time exists independently, and we can’t tell it what to do—but until I read Full Engagement I didn’t have a good alternative.

In the book, the authors show that instead of trying to manage time, we should be conscious of managing our energy. At different points in the day we have more energy than others, and we’re also motivated to do certain things at peak moments. They key is working with what you’ve got, and planning your work times around when you expect to have creative energy. (This is also a good reason to never answer the phone—but that’s another story.)

Whenever I try to motivate myself to do something, I encounter a great deal of resistance. Whenever I do what I’m already motivated to do, I work much better and get much more done.

***

At TEDx in Pittsburgh I talked about the idea that many of us live our lives waiting for someone else to give us permission to be ourselves. I know that I’m wired for an active life and I wouldn’t be happy with anything less.

That said, I do get tired—sometimes even exhausted. On Thursday I came home and slept away the afternoon. Friday was OK, but on Saturday after yoga I took another two-hour nap. All three days were low on productivity, and I think I still need a bit more recovery time.

It’s good to rest, in other words. But I think it’s even better to have something to rest from. With that in mind, I’ve got more adventures planned, very soon. But first, another nap. zzzzzz…

How about you—how do you rest and recover?

###

Image: Esther

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

What, you didn’t know that Luciano Pavarotti was huge on Twitter?

Oh yes. Or at least, he could have been.

See, every day I talk with various people about their projects. Inevitably, I hear a lot of questions that are rooted in this premise:

“How can people give me their attention?”

In other words: “How can I get more for myself?” The more in question varies: interest, customers, website traffic, subscribers, money, whatever—but it always relates to an increase in focus on the individual.

There’s nothing wrong with any of those things. I’d like more too. But motivations can be interesting predictors of success. The more that we want tends to come along when we give more, but when we give because we want to receive, it doesn’t always turn out so well.

If it sounds complicated, it’s not. Here’s the secret:

Some singers want the audience to love them. I love the audience. -Luciano Pavarotti

Interestingly enough, in the business I’m in, I’ve noticed that almost everyone who is successful in the long-term lives by this lesson. Yes, there are a few exceptions. But you can usually tell how it goes down within a few minutes of meeting someone—and these days, you can “meet” someone whether you’re in the same place or not.

Therefore, the better question to ask is:

“How can I give more?”

Sometimes I’m ashamed at my giving / receiving ratio. Look at that guy Jonathan Fields! He’s always saying nice things about me. I can’t keep up. I wrote him and said, “Dude! Slow down. You give too much.” (To which he said: “There’s no scorecard.” Of course he would say something like that.)

Look at that guy J.D. Roth! He writes about me all the time, even knowing that some of his more conservative readers think I’m crazy for spending my money on flying to Cape Verde without a good reason.

Quick update on that: British Airways is still on strike, but last night I made it back to London on a charter flight operated by EuroAtlantic. I’d never heard of EuroAtlantic before, but BA switched me over to them and it worked out OK. Next stop: Sal Island.

These people, the Jonathans and J.D.s of the online world who give back all the time, are incredibly rich in goodwill. I feel like I am permanently in their debt, and it makes me want to give them whatever it is I can give.

And of course, it’s not just the famous people. It’s Everyone Else. All of YOU who read from more than 100 countries now. Every day I look at the comments, the emails, the trackbacks, the fun things everyone is doing and think… am I really giving enough? How can I give more?

Understand: there’s nothing wrong with promoting your thing, asking for help, making a living. I don’t even think there’s anything wrong with wanting more.

But I figure the first step is to adopt Mr. Pavarotti’s perspective. It seemed to work out fairly well for him, even without a fan page or a LinkedIn profile.

Give back. Show love. If you want to change the world, love the audience.

What can you give the audience?

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Image: AA

It all started when I was feeling overwhelmed in the development of Empire Building Kit, my biggest business project of the year.

I’ve been working hard on it for weeks, but with all the material I’m putting in, I could see it would need more time.

Then I started making plans for the big trip I’m starting later tonight. I’ll be in Central America this weekend, enjoying cheese empanadas and café con leche while working from the road. Then, I’m going across the Atlantic for visits to the Ukraine, Cyprus, and Cape Verde. On the way back I stop off in Pittsburgh for a talk before continuing home.

I know it’s a very full itinerary. For everyone who’s new here, my theory is: to have a big life, do big things—but wait, more on that in a moment.

From Pittsburgh I fly to Chicago, but I wasn’t able to find a flight back home to Portland the next day. Thus I had two problems—when to launch the Empire Building Kit, and how to get home from Chicago.

I was telling Jolie all about both of these problems right before I went to Austin. “Why don’t you take the train?” she asked.

I looked at her like she was crazy. “From Chicago to Portland? Do you know how long that would take? And besides, it’s Amtrak.”

(No offense to anyone who loves Amtrak, which I assume would include anyone who has never ridden a train anywhere else in the world.)

But while we were talking about the need to push back the Empire Building Kit a couple of weeks and how to get home from Chicago, I agreed to look at the idea of taking the train. And guess what came up! Check this out.

That’s right…. the name of the train from Chicago to Portland is EMPIRE BUILDER. Wow. Talk about coincidence. It got me thinking about a crazy idea… but then I thought, no, that would be way too difficult and way too unrealistic.

The next day, the UPS guy knocked on my door to deliver a package. Various travel companies have been sending me free laptop bags recently, and this was the latest shipment. I don’t usually accept free stuff, but I decided in this case I’d do a review if I liked one of them, and give away the ones that aren’t for me.

The name of the bag, I kid you not, was EMPIRE BUILDER. Wow. OK, I decided. I am now officially paying attention. Even though I don’t pitch stuff on behalf of big companies, I figured this deserves a mention.

Then I realized something else: I’ll be coming home close to my birthday, which also begins the three-year countdown to visiting my final 62 countries. I could return to Chicago, take the EMPIRE BUILDER train with my EMPIRE BUILDER bag, and launch the EMPIRE BUILDING KIT while riding through North Dakota on my 32nd birthday.

A crazy idea, yes? So of course I decided to go for it. What could go wrong, besides everything? Remember: it’s almost always better to do something. It will be a good story either way.

Enter J.D. Roth

Then I decided to make it even bigger. I called up my friend J.D. Roth, whose book is launching that same week.

“How would you like to launch the book in Chicago, and then do media interviews from the train for 46 hours on the way back home?”

Mr. Roth thought about it for about five seconds and said yes. (That’s why I called him! I knew he would.)

So that’s the plan. I wanted to find a way to make the EBK launch a fun experience for everyone, including all of the people who don’t need it or aren’t otherwise interested. Now we have a fun story, a party in Chicago, and one tired non-conformist writer by the end of it.

Here is the schedule:

Now until early April: Chris on the road in various countries, frantically wraps up the content for EBK, media stuff in Europe, etc.

3-April Return to the U.S. (SID-LIS-MUC-ORD-PIT)
4-April Speaking at TedX, Carnegie Mellon edition
5-April Chicago meetup (RSVP here to get on the list) + book launch for J.D. Roth
6-April Embark on the Empire Builder train with J.D. and the Empire Builder bag
7-April Amtrak Birthday Party + Live Launch of EBK somewhere in North Dakota
8-April Return home, sleep for five days

The Universe and the UPS Guy

Perhaps the universe does not bring a UPS guy to your door with the name of your next business project emblazoned on a complimentary laptop bag. Unless your project is called Cascades, Eurostar, or ViaRail, there might not be a train named after what you’ve been working on for months.

But look around! You never know where you’ll find synchronicity and encouragement. Try stuff out to see where it leads; focus on telling good stories with your life. My friend Charlie Gilkey made a shirt that expresses this idea well.

I read the new book Rework on the flight back from Austin last week. My favorite story was how they didn’t have a way to get paid for a project that billed customers every 30 days, so they kept putting it off. Finally they just decided to launch and then figure out how to get paid sometime before the 30 days ended. The clock was ticking, they knew they had a month to get it done, so they figured it out right before the end.

And now the clock is ticking for me: I fly to Miami tonight, and off we go. I’ve got 19 days to make this work. I’m simultaneously scared and excited, which I figure is a very good sign. Here’s wishing you well as I head out to Miami and beyond. Next stop, Nicaragua, then everything else.

Your faithful writer,

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Image: PB

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.

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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.

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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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