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Mistakes on the Road to Creative Freedom

I’ve been self-employed for more than fifteen years, but it hasn’t always been easy.

I once had the bright idea of selling a golf membership service for $1. (It was actually a very bad idea—no one told me you can’t make money on $1 per customer.)

Another time I tried to launch four projects on the same day. (Another bad idea—none of the four projects did well because my attention was so divided.)

When I wasn’t burning down houses as a teenager or failing to ever learn algebra, I was fumbling along from project to project. I always made a decent living, but it was hardly strategic.

It’s always a journey, natch

You don’t have to have it all together when you start. You start from where you are, and—this point is critical—you get a few things right.

John Jantsch put it best:

“Behind every great business is an entrepreneur who’s pretty sure she’s screwing up.”

The fear of screwing up rarely goes away forever, but you have to find a way to separate it from your ability to make progress. You create the right product or service. You find a market of people, even a small one, that wants to pay for it.

I always tell people who are beginning a creative career to go back and look at the early work of artists they admire. If you come across a successful blogger, designer, or artist, especially one who’s been able to generate a full-time income from their creative work, it’s easy to be intimidated.

That’s why you should go back to the beginning—see where they started, and see how it all began. When you do that, you’ll be able to see the progress along the way, most likely including a few mistakes.

In my case, the compass points are independence and gratitude. Much of AONC has been built on an anti-authority construct, the idea of being “self-employed for life” and answering to no one. I still believe in this value. There are far too many people who feel trapped in dumb jobs. They need to escape!

But I’ve also tried to branch beyond “anti-authority” to being for something. I want to contribute something. I want my life and work to matter.

Forward, Onward

The other part of obtaining creative freedom is sheer perseverance. Just kept going!

Seth Godin once talked about his failures in the context of eventual success:

“If I fail more often than you, I win.”

That’s how I feel. Failure sucks but failing to try is far worse. The life of creative freedom is worth fighting for.

***

In just under two weeks we’ll be releasing our biggest Unconventional Guides project in more than a year. The goal is to help artists, designers, crafters, and “makers” of all kinds achieve creative freedom through self-employment.

A few years back I launched the Empire Building Kit, a resource that focused more specifically on online business. This new resource is essentially an Empire Building Kit for creatives of all kinds. If you’re a designer, artist, crafter, or “maker” of some sort who wants to sell your work—not just make it for fun—this project will show you exactly how to do it.

I haven’t been this excited about a new resource in a long time. On Monday we’ll share more of the lessons from some of the people featured in the new project, and next Thursday we’ll have a complete sneak preview along with a fun giveaway.

Question: What do you think about creative freedom? Have you made mistakes in pursuing self-employment?

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54 Comments

  • Tyler Hurst says:

    My biggest mistake? Thinking that because I could figure anything out, that everyone I wanted to work with could, too.

    Teaching is as important as doing.

  • Biggest mistake? I waited too long to start. Thanks for all the value Chris…and the transparency.

  • Kimberly says:

    Hmm, mistakes in pursuing self-employment? I’ve made dozens! Probably one of the biggest on the list was refusing to spend a dime on training in the beginning because I thought I couldn’t afford it. But once I decided that I was worth making an investment in and so was my business, things started to change – I got more traction and started earning more of the green stuff. I had to sacrifice some things to make room for some of the training I ended up buying, but the ROI has made it worth it. One of my highest values is creative freedom, so whatever it takes to be “the decider” in my own work life, I’m pretty much willing to do. : )

  • Tisha says:

    I think creative freedom is something most people seek, whether they know it or not. I also think it’s something a person has to serioulsy sit down and define for themsleves, because it’s probably a little different for everyone. I read a quote somewhere that basically said don’t compare your beginning to someone else’s middle. I try to keep that in mind whenever I make the mistake of comparing myself to others. And just like you wrote, I’m finding out that “you don’t have to have it all together when you start.”

  • Anita Chase says:

    I just saw a new documentary film a couple days ago called “An Honest Living” by Jordan Freese. It is an independent documentary that “follows four Chicago based artists as they reveal how they dance the line between artistic passion and the need for commerce. The idea of passion versus commerce is seen through the eyes of four very distinct artists. Each character has a unique drive and artistic conviction that sometimes vastly contrasts the trades they use to support themselves financially. They need to eat and pay rent, like we all do, but how does one make a living and still keep their identity as a true artist?” I don’t know anyone connected to making the film, I just think it was great for anyone considering this path.

    Watching that film and then seeing this post is feels like someone poking me in the brain to look at my self-employment options more and come up with a better plan of action. I have pursued self-employment at times, but I would say my biggest mistakes have been being too tentative, and letting other people hold me back with their fears. Onward!

  • Joe Flood says:

    I still haven’t figured out self-employment though I’ve tried a couple of times. The interesting work part I got figured – it’s the how to make money part I haven’t gotten down yet. The next Unconventional Guide sounds like it would be perfect for me.

    Megan McCardle has a new book coming out on the positive aspects of failure, how it is a learning experience. She describes all the ways that she’s failed and how they led her to success. Interestingly, in surveys a lot of people say that their failures – getting fired, divorced – were the best thing that ever happened to them. Here’s my review of The Up Side of Down http://joeflood.com/2014/01/26/up-side/

    It’s great that Chris speaks frankly on failure. I know a lot self-employed folks. Behind the dream of freedom is usually a lot of challenge and hard work.

  • Amanda Foltz says:

    Love this post. I so do look at all those who have “made it” and wish I could be there yesterday. Even with how challenging pursuing the dream of self employment (not just self employment but free to do what you want, work when you want, be who you want). I still find my self waking up every morning, dusting my self off and doing it all over. I was born to be creative and I know some day my talents will pay off. Not just for me but, I believe I have something special to offer the world.
    Mistakes: Are there ever mistakes if they lead to success?

  • Ben says:

    Amazing! Thanks for sharing.

    My biggest mistake: Juggling Business ideas in my head since I was 16 instead of actually “DOING stuff”, instead of just starting.

    It has never worked out as planned it in my head so far – so it´s never early enough to actually start doing.

    Best,

    Ben

  • Ree Klein says:

    This really resonated with me, Chris. I am 55 and worked in Corp America for, well, a TON of years. But all along there was this undertow telling me I should be working this hard for something more meaningful to me.

    Last year I left Corp America and started my business, but I’ve had trouble monetizing it. I’ve even thought of giving in and going back to you-know-where. Just yesterday an opportunity arose when an HR exec I used to work with suggested I come work for her (a good and reliable income).

    But I just couldn’t give up on my dream. It feels like a failure in that I haven’t been paid for all the hard work I’ve put into it, but reader comments and some emails from readers have been payment enough for now.

    I’m excited to attend this year’s WDS because I do believe that training and connecting with like-minded creatives is essential to success. Thanks for creating programs that spark inspiration and help push failure into a corner where it belongs!

    Ree

  • Lucy Chen says:

    I’m excited about this one, too!

  • Dan Quizal says:

    I have been a on-and-off self employed entrepreneur since I was 5 years old. When I was in college, I tried working a JOB, but didn’t like it, so I became a dentist. Good money for over 25 years, but quit that too. Helped create the internet (1993) and loved that. Still do that, but my wife thinks that it is just a waste of my time. Takes a lot of fun out of it. Wish I had more of a partner here. Oh well, just keep plugging along from Panama. Will eventually make it as a internet marketer, helping others with their success.

  • Scott says:

    Failure #1: 1990 – Tried to hang a shingle and be a self-employed “rookie” attorney…bonk!

    Failure #2: 1996 – Left the profession to become part-owner and manager of a golf vacation business run by my mom’s then crooked husband…bonk!

    Failure #3: 1998 – Started a boutique mergers and acquisitions advisory, road a wave of tech deals until the .com bubble burst and I was caught with more overhead than the deal-flow would support…bonk!

    Failure #4: 2001 – Finally landed a deal in Costa Rica, managing the sale of a for-profit private university. I did close the deal, but in the meantime my personal life fell apart and I got divorced…bonk!

    Failure #5: 2004 – Moved to Costa Rica and started another vacation design and management company, but once again ramped up overhead due to grossly over-optimistic sales forecasting…bonk!

    Failure #6: 2004 – 2012 – Relied on others to do my web development and design and never learned the craft and the experts who helped me never did either…bonk!

    Failure #7: Started blogging back in 2006, but building a mailing list never occurred to me, so when I decided to get serious last year, I had to start over…bonk!

    Do I qualify for the prize?

  • What do I think about creative freedom? It’s the most important thing I’m pursuing at the moment!

    Mistakes I’ve made:
    – Trying to create a business in a niche that I wasn’t really informed about, so when the product and site was ready and I had to start marketing, I didn’t know where to begin, FAIL
    – Hire a marketing agency to help me when I haven’t figured out what works in my business myself.
    – Spending too much budget on PPC, way too much, with no returns.
    – Thinking the government cares about what you do, they don’t, they want everything to stay the same, or at least not change to radically too quick
    – Lending money and investing it wrong, it was a pain to pay everything back through a regular job

    all mistakes I positively learned from, though. Only through doing these I learned more and more about what is going to work and what isn’t, and what you need to do to make something work.

  • Natalie says:

    Ah, this came right in time. I just lost a big client, was WTFing all over the place, and now have a little more perspective. Thanks for that.

  • Kate says:

    I think we are often simply scared of embarrassment from some type of public failure. It’s ego. Once I realized my real fears in life were that something would harm my kids or I would lose a body part, I was able to create a successful public radio show (Live Wire!Radio). Eight years later I was scared to leave, but did. Again, I knew no real tradgedy was going to occur. I’m a freelancer now and everyday is a bit scary. But it is scarier to contemplate a life without joy and meaning from my work.

  • Mark says:

    So can we pre-order?

  • Aprille says:

    I’m struggling with how to make money. There’s education involved, as Tyler said. I’m also trying to mold a bit of a new space, so it’s taking longer to ramp. I tell people it’s more art project than business – I’m proving out my case. Then I need to package it and figure out how to sell it.

    So the question becomes – how does this get to a point where enough money comes in from grants or customers to keep us above water, when I need to get that other FT job to stay above water until then?

    Mistakes were thinking I had a model that could roll from day 1. I need to lay more groundwork. Thanks for this post, though – I do try to keep reminding myself that the people I’m looking up to took a bit of time, too.

  • Lara says:

    My business is now 1 year old. I feel that mistakes might have been in the pricing area – charging what a template website costs for a bespoke service for example. But it has given me so much happiness and freedom. I am just aiming on getting the income to match the happiness now!

  • Joana says:

    “If I fail more often than you, I win.” — this reminds me of Samuel Beckett’s quote tatooed on the arm of recent Australian Open champion Stanislas Wawrinka: “Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.”

    There’s this other quote (can’t remember the author) that says: “Success is the ability to go from one failure to another with no loss of enthusiasm”.

    Yeah… seems failure really plays a huge part in success 😉

  • Ree Klein says:

    I just had to leave a comment for Scott who left the comment above listing his series of failures in chronological order.

    Scott…I know it wasn’t funny when it was happening, but your list and the way you described each “Bonk” had me in stitches. You should win the prize and more importantly, I’m CERTAIN that success is just ahead for you. You obviously haven’t forgotten the lessons and can turn them into gold.

    I’m cheering for you!
    Ree

  • Doug Armey says:

    Mistakes and failures are part of the game of living life on on your own terms. The key is to make sure the failures aren’t terminal. Taking small consistent steps, making small but relentless tweaks helps insure that the inevitable mistake doesn’t end in complete irreversible failure.

    If you don’t survive the failure you don’t get to keep playing. Keep the failures manageable so you can get up and keep going.

    Great post and reminder.

  • MK says:

    Before entered ANOC, I thought the creative freedom is just something being exaggerated, but after entered ANOC and found out something that I want to do to, I am trying to reach the goal now, and I try to promote this idea with my friends, Everyone really needs to free themselves to fulfill their potentials & creativeness.

  • SO many mistakes! Not charging enough, not putting tax money aside, working with the red flag clients, hiring the wrong contractors, starting a biz with the wrong partner, building a biz around the wrong thing, failing to have contracts, and on and on. It’s so important to share and be transparent and I love your advice to look back at where your inspiration began.

    I laugh when my coaching clients put me on a pedestal and promptly explain to them how I’m human just like them… there’s usually an awesome failure or oopsie story to go with it. I’m not perfect, and having others think I am because my business is growing doesn’t serve anyone! Feeling like you have to be perfect hinders creativity for sure.

    Thanks for this great post!

  • Kola says:

    I’m commenting because of Scott and Ree. I don’t even know where to start with listing mine but you both certainly brightened up my day today. So thank you : )

  • My failure list:

    Trying to figure out everything on my own.
    (my theme of this year: cooperation)
    Procrastinating on important phone calls.
    Losing focus because of an overload of ideas.
    Working too hard, and not taking enough rest, and time in nature.

    so thanks Chris for bringing the weak points back into remembrance! And Joana, for citing the quote: “Success is the ability to go from one failure to another with no loss of enthusiasm”.

  • Fraser says:

    Eight years ago I blew my life up while trying to get a new business of the ground. I lost everything. A very painful experience indeed. It took me over seven years to take the lessons I had learnt and vernture out on my own once more. It will probably be another two or three years before I earn any money from what I’m doing now – blogging about my adventures cycling around the world, and writing books. My first priority is to raise enough money to build a new school with Room to Read.

    In my experience failure occurs to point out what you need to pay attention too. You simply can’t grow without it.

    Thanks for sharing Chris

  • Damien Jones says:

    I have dabbled with self employment since I left College in 2001 being driven to make a living on my terms so I can have time to make music. I became disillusioned with music education when a professor told me he worked 7 days a week as a musician and teacher to make $60,000 a year. I didn’t want that. Now I work even harder doing something I don’t love for the same amount of money.

    I have designed many companies and products that I either failed to start or failed at in general. I don’t mind failing, it’s the starting that has been difficult. One thing I do is run an arts funding org called MK Eat. I started a podcast in order to build awareness and connect with artists while doing something for the community. Last night was the first recording and it was the 3rd time I rescheduled and still had a part of me that didn’t want to go through with it. I am really glad I did. We collected clothes for a homeless shelter and set the stage for what I think will be a positive show.

    By reading the post, the comments, and checking out the information on the doc that Anita posted, I feel energized. I’m ready to do more with my company than occasionally write a blog post.

  • M. Catlett says:

    It boils down to experimentation. No educational summary that worked for one person or one business will work in the same way for another person or business. The times change, the environment changes. Our best paths cannot be prescribed, we must determine them through trial and error. Certainly, I’ve a long way to go myself, but couldn’t agree more with the overriding sentiment. Hike up the next hill, scan the horizon for the next hill to climb, and repeat. That’s how people end up sitting on top of mountains.

  • Toni says:

    My mistakes on the creative way:

    1. I believed that I was the artist and I could live for it.
    2. I realized that I was not the artist and left that way.

    Now I want to reach, with help of your blog, creative freedom. For me it means to free the true artist, which lives in myself. I hope it is not my next mistake.

  • Akinsola says:

    I am appreciative of a point you made,I could remember a time that I started reading your blog right from the first post. It does not matter how slow you go so long as you do not stop. — Wisdom of Confuscius

    I think the first thing you learn is to be persistent whether you want to or want not.

  • Rudiano says:

    I love the idea of creative freedom. Jobs tend to suck the life out of me. The last one I had messed up my health (because of stress).I have been struggling ever since.
    I have been dabbling in all sorts since. Blogging, network marketing, free lance writing, fiverr selling, music selling… My mistake is probably that I’m not focusing on One thing….but that’s hard when you are living paycheck to paycheck!

  • Oh, I’ve made my fair share. Thinking people would want what I’d offer without actually offering it to them. Thinking I could charge premium prices just starting out (sometimes you can, sometimes you can’t). Thinking I had all the answers.

  • Chris says:

    Yeah, we use to get intimidated because we see the successful people in their glory moments and not look at their past failures and struggles. We tend to overlook their progress and the amount of time it took for them to get to where they are right now…I feel the same way many times, but then I say to myself that I need to regain focus on what I have and on what I want and to keep persevering…

    Wonderful touch Chris!

  • Aldona Kmiec says:

    Great to learn. Due to expansion and setting up a business in a new country, I took a risk and dived into too many serious long-term projects, all at the same time. When the feeling of burning down finally came, I learnt to become more selective with my time. Stress didn’t leave me for months..

  • Bastiaan says:

    Hello Chris,

    I want to thank you for this very inspiring article. I just started a blog as a business and it is very overwhelming. I look at all the big and famous blogs and then compare them to mine. It makes it frustrating because I want to be were they are as soon as possible.

    I try to read everything I can. Books, blogs, articles.. everything. If you want to go somewhere to fast it overwhelms you. And I am pretty afraid to make mistake.

    Thanks for putting things in perspective. I now realize that every blog/business needs its time to grow. If I can learning from my mistakes and make my blog a little bit better every time I will eventually grow as big as the others.

  • Marti says:

    Chris, I’m just getting ready to start down this path. You’ve been part of my evolution. You and many of the people I have met through WDS. Get doing what you are doing. You are making a difference!

    Marti

  • I have made so many mistakes in my ventures toward self-employment that they could have a book about me to share all the many mistakes to avoid. I love creativity because it is an endless flow that makes me feel alive. I write, journal, blog, sing, paint, collage, cook and coach and do it all creatively and intuitively.

    The interesting outcome though is that I have learned there is no failure, just feedback and that I am not my mistakes or my successes. I am spiritual being having a human experience and trying to enjoy as many moments as I can be present to. Then life can be the purest joy.

    Thanks Chris for your inspiration.

  • I think my main mistake was staying in a traditional job for too long because I thought I had to. I had reasons: immigration (I am Swedish and I was working in the US), career progression, financial reserves, ego, etc. But taking the leap (which initially took the form of a 12-month travel and service tour around the world) with my wife, I don’t think either of us is upset about our new, entrepreneurial route. It was hands-down the best move we have made to date. This may change in the future but so far I feel that making money through entrepreneurial means can force growth and success that would not have been possible back in the 9-5 environment.

  • Aloysius says:

    Twice I’ve failed because I was too successful – it was time to delegate; time to hire help. But it never even crossed my mind. I just felt overwhelmed. Well I had a right to since I WAS overwhelmed.

    Re-working my non-existent business plan would have kept me from crashing and burning.

  • Philipp says:

    Mistakes are good, as long as you are able to learn from them. My biggest mistake? Trying to start a decent career while building a business on the side…

  • Heard this looong time ago…… the definition for Creativity is NOT to always do something completely new….
    After all…. There’s NOTHING new under the Sun??? Whaaaat *o*
    Yup….
    The Definition for Creativity is: To do OLD things in new WAYS! And THAT in itself is a tremendous challenge!…. I’m still -after 60 years- working on it…. 🙁 🙂
    But, I stopped beating myself up for not having been successful….

  • Writing a book before blogging. Just wrote it blind (although has a mentor whose been published), on pure passion and because I had a message I just had to share but without an in depth awareness of how the internet marketing thing works.
    Almost 2 years after releasing on Amazon Kindle still learning about building an audience.
    My lesson?
    There’s nothing harder than forging your own life. But nothing more rewarding.

  • Barbara says:

    My biggest lesson was when I realised that building up my own business was actually a personal journey – with lots and lots of things to learn through my own experience – and not just applying other people’s recipes and expecting them to work out.

    To me, mistakes are just a learning process, nothing negative. 🙂

  • Mac McGowan says:

    I’ve been doing creatve “making” for a living since 2005. Plenty of failures along the way but I have a good reputation for quality craftsmanship and good customer service. My biggest failures are based on not being very nimble to protect the product and the process -or adapt to new ones – when the offshore knockoffs start arriving. It’s inevitable and I need to move more quickly to position myself in the market to withstand that onslaught.

  • I think my biggest mistake is that sometimes I try to find the perfect idea… and so I don’t start as many new projects (not a problem in and of itself, but you know what I mean)… In a way, it’s kind of like the fear or failure, and fear of not having the right idea before I start something!

  • In the past year I’ve finally started realizing that what I once thought were huge mistakes were actually major accomplishments. My biggest mistake throughout it all was beating myself up for it when I did make the mistake. Had I known then that the mistake was going to lead to a future triumph (whether personal, business or both), I probably wouldn’t have been so ruthless.

  • Eli Griffith says:

    Biggest mistake – keeping my day job.

    My partner/advocate advised me to focus 100% on my own work, but instead I followed the common advice to keep the day job. It was a tremendous mistake financially and productively.

  • Karolinka says:

    Biggest mistake? Waiting too long to start, thinking I’m not good enough yet. Finally gathered courage last month and I’m off!!!

  • Manohar says:

    I am very excitedly working on a on online project . I plan to launch it really soon. I know the customer and customers customer . I think it will succeeds because its going to fill a gap in the market and it will help the customer as well as customers customer.

    My learning failure was launching a service which I knew was not going to be easily accepted , however I wanted to do it to motivate myself of going ahead with an Idea and over coming hurdle of just thinking of an idea and not following it up to execution. I very happy I did it. As expected it did not click but it boosted my risking taking capacity.

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