Lessons from 4 independent years

In 2003 I quit my management job at Microsoft to try to live by writing books, teaching and public speaking. It was the scariest decision I’d made in my life and here on the other side, about 4 years later, is what I’ve learned. If you believe life is to be explored, here are notes from a work adventure. There’s no amazing new theory – you may have heard all this before, but here it is, in first person.

Emotional & personal lessons:

  • Big decisions divide friends. In 2002 I talked to friends/family, pitching the idea of quiting to write. Their responses were surprising: Some were mad I was throwing away (their words) what I had. Others told me, exclusively, things to fear (the attack of the “what if’s’). But some listened and probed to help me sort out my feelings. I learned the difference between being close, getting advice and having someone’s true support (where no matter what you choose they offer their energy in your service). I learned the people closest to you, aren’t necessarily your best supporters, and you wont find your true supporters until you make decisions big enough to call them out. If you do something big, you will divide the people in your life in unexpected ways: the truth comes out.
  • No one will tell you what you’re capable of. No one told me to quit. No one told me to write books. None of the interesting things I’ve done started by someone telling me “you should do X.” or even “you are capable of doing X”. I’d been thinking about this for years but was waiting for some message from above to show up like the billboard in L.A. Story, saying “Scott. Now is the time. The universe has your back. Go do it”. But I’m still waiting for that. I’ve learned that not having support from others is not a reason not to do try something. I have to do the work, so my belief is enough.
  • Network is everything. Independence is a funny word. Yes, I am my own boss, but because I’m solo I have a huge network of people I depend on to make a living (including you, dear blog reader). For writing it includes publishers, editors, illustrators, and most amazingly, people willing to spend money to read things I write. For speaking, it includes corporations, conferences, and individuals who spread the word about my talents in front of crowds: all of whom I need to get new engagements and keep this going. To be on my own actually means my fate depends on more people than it did in a corporate job, it’s just a more diffuse dependence.
  • I miss collaboration and having someone to blame. I have more work freedom than anyone I know. But the price is psychological. 1) I don’t have a boss or bureaucracy to blame (a surprisingly popular psychological tool). 2) I can’t leverage the passions of co-workers, or rally with a team in the last days before a deadline. For all the freedoms I’ve obtained, there are new kinds of stresses: it’s a great trade, but not a fantasy wonderland. I’ve considered taking a part-time job, or being some kind of part time “wanna-be guru in residence” somewhere, to get a couple of hours every day of energy exchange. Just to be around teams of creative people a few hours a week, being a sounding board and giving advice, might boost my own total creative output. (I know, I know, boo-hoo, writerboy is lonely… how sad – I’ll stop whining now, and hit you with the practicalities).

Practical stuff:

Here are some of the most frequently asked questions I hear.

  • Leave on good terms. I bet you know someone at your place of work who quit to do something else and then came back after a year (possibly for higher pay). If you quit, make sure to quit on good terms. Don’t just give 2 weeks or use your leaving as a chance to vent. Make your previous job into your last resort backup plan. If you stay in touch with your former boss or co-workers, you’ll have a lifeline in your back pocket should your independence fail. Leaving on good terms also may enable you to use your previous boss/coworkers as your first reference.
  • How to get your first client. There is no excuse for not getting a first client: work for free. This applies to writing, consulting, speaking… everything. If you can’t find anyone who will hire you for free, make up the assignment and build a portfolio (Redesign a famous website, critique a well-known piece of software, re-design Central park, etc.) With youtube & blogs the barrier to entry for talent is ridiculously low. When you do get a free client, and do a great job, you now have your first reference, increasing the odds the next client will be for pay. Pick free clients that have friends, or ask them to help you with referrals in lieu of payment, or the right to publish online the results of your work for them. If you are doing excellent work, eventually people will pay you to do it. And while you are waiting for income you are building a great portfolio.
  • Plan for a lean 6-12 months. It took me a year to figure out the business of public speaking and how to find clients. It took more than a year, and dozens of rejections, to get my first book deal. I expected this when I quit and had my finances set up to handle it. I worked out a budget and waited until my savings were sufficient to prevent panic for at least a year. I didn’t want to be 6 months in and struggling, and cop-out because I could claim I was out of time. Slow ramp-up for independence is unavoidable. Many small businesses fail within a year, and I suspect many simply didn’t plan for 12 months or more of ramp-up time.
  • How to decide your fees. This is easy: find a competitor and ask them. There is no shame in asking people their rates. If they don’t tell you, ask their clients. Ask, ask and ask until you have enough data to make a judgment as to where you stand in the range of experience and quality. If you charge hourly rates, make sure to include your cost of living. Your rates must include cost of living, plus advertising, finding clients, and other activities that consume time. It’s smart to budget for a lean year to ease the burden of finding a revenue stream. You may discover your revenue doesn’t match your life expenses, but if you’re lean to start you’ll have more time to make adjustments.
  • Networking? Live by lunches. I know just about every decent eating establishment in Redmond/Bellevue/Fremont/Capital Hill/Seattle. Why? Well, first of all, there aren’t that many (ha ha). I have lunch and coffee with people all the time. It’s a substitute for having a hallway of interesting people to chat with and keeping some regular opportunity for the unexpected to happen. Never know who knows who, or what friend shows up, or what advice I might get. It’s ironic, but being independent depends on being visible. The web and blogs are powerful, but meeting someone over a meal makes a stronger connection than some e-mail or swapping of links. You’d be surprised at who will chat with you or give you advice if you ask nice, pick a good place and offer to pay.

Mistakes I made:

  • Not leveraging biznik.org. My timing was off – I quit before this group was at full-speed, but what a missed opportunity! This community of independents is super strong, supportive, and centered on workshops, events and socializing. Dan and Lara, the founders, are awesome, super positive community building rock-stars. I’m not a joiner, but what these guys have done, and their genuine benevolence and passion for it, is an inspiration for independents on it’s own. If I were thinking of going-indi now, this would be the first organization I’d sign up with.
  • Not having a a menu. I’m a versatile guy, and I figured my many hats would be a big asset to clients. Wrong. Conversations would go like this. Them: “Hi Scott. We want to hire you. What can you do for us?”. Me “Everything!”. Them: “Oh. Hmmm. Ok.” And then I’d never hear from them again. All consultants must have a simple menu so clients have a basis for a conversation. Pick the 3 or 4 services that are strongest, or most applicable based on the client, and focus on them. It’s always possible to propose things off the menu (“here are my specials”), but make the conversation easy for clients, including offering a price sheet.
  • Consulting vs. Speaking . When I quit I thought the best business for me would be consulting. Wrong. In my first year I did both, but found the dynamics of speaking much better for everyone: it’s clearer what my value is, defining the problem they want me to solve is easier, and after a successful speaking engagement, it’s much easier for clients to use me for consulting work. These days I do way more speaking and teaching than consulting (I’d guess it’s 80/20%): it’s often better, simpler, and more rewarding business.


  • I’m still doing here! Doing this! I had no idea what would happen when I started. I’d convinced attempts are the most important thing, as I want to live a long life of attempting to do interesting things, no matter what happens. So I’m as surprised as you are to be in whatever position you think I’m in. The fact I’m writing this post, and have all this stuff to say about work independence, is surprising too. My lifestyle is entirely unexpected.
  • I don’t talk much about design anymore. My claim to fame in 2003 was advocacy for all forms of design and user experience work. But publishing a book creates a wave of attention around whatever the book is that dominates whatever attention I had before. In 2005, I was mr. project. In 2007, I was, and still am, seen as innovation expert dude. I’m sure if my next book is about swiss cheese, and it does well, I’ll be speaking at cheesemonger events. Fine by me.
  • The sweet spot of popularity . I’ve found this nice little place where I get more than enough offers for work than I can take, but no so much that I’m buried by requests or attention. For a couple of hours every week I get to have my rock star moments as mr. guru or talking head, but the rest of the time, I’m just a guy who writes and plays with his dogs. I don’t know if I can sustain this sweet spot, but I hope I have the wisdom to seek only as much attention as I need to keep my independence.

Hopefully I’ll keep this going at least another 4 years, and have more to offer in the life lessons department. If you’ve bought my books, hired me, or forwarded links of my stuff out to others, thanks for making an interesting life possible. I have big plans so stay tuned for more.

Happy to offer advice – 4 years isn’t that long, but if you think I’ve learned something that can be of use, ask and lets find out.

17 Responses to “Lessons from 4 independent years”

  1. Jason Abate

    What a great summary Scott – lots of good advice in there. One addition from my background – when deciding to leave my full-time, comfortable gig about a year ago to start my own company, I started by figuring out the absolute worst-case scenario and discussing it with my family.

    This helped to put into concrete terms lots of amorphous fears and really put things in perspective. In my case, the absolute worst case was to blow through some savings, possibly have to sell our house and move, and get a full-time job again. Really not that bad – still have my family, still have my friends and associates, etc.

    Once I looked at things from this perspective, it became a pretty obvious choice to make the jump. One year in, it’s too soon to tell for sure where things will end, but so far it’s looking promising!

  2. Gustavo

    Hi Scott,

    First time I comment in your blog, just to say, fantastic post!
    I’ve just bookmarked it in my all-time best advice texts.
    Thank you very much!

  3. Adwait Ullal


    There is also the matter of administrivia that should be taken care of up front … as well as on going (like medical, quarterly SE taxes, etc.) that must not be neglected.

    I’ve been doing it (consulting) for the last 12 years and enjoying every moment of it.

  4. Christopher Mahan


    I bought “The art of project management” and “the myths of innovations” (which btw had great resale value) and I’m looking forward to “getting things done”. Thanks for writing great books and being candid about the experience.

  5. Eric Nehrlich

    Congratulations on four years of being independent. I’m starting to play around with the idea of finding a way to work for myself, and this post is great inspiration. Thanks for all of your sharing of advice and the great work that you do!

  6. Jordan

    Scott, thank you for the post. It is inspiring, down to earth, and practical, and I really appreciate that.

  7. Janusz

    Especially “not having a menu” was impressed me because I met such situations in my experience. I can’t sell everything. Who buy everything? :)

  8. Pat

    Very intersting post on a much interesting blog.
    I’ve been subscribed to the feed for months and…may buy your book soon :-)

  9. Simon Wardley

    As someone who is building their own fledgling career in speaking, consultancy & writing, this is a truly inspirational post.

  10. Working Girl

    Great advice. So true what you say about asking the competition when deciding what to charge. When you’re freelance, you feel as if you don’t have co-workers. But really your co-workers are other freelancers.

    The thing that bothered me at first about working on my own was that I had to do everything. I was the mailclerk, billing department, etc.

  11. Kevin

    Scott, congrats on such a successful 4 years! I remember taking your training classes at MS years ago and hearing you were leaving to work as a consultant. I admire what you’ve done.

  12. Berthold

    Thank you for writing this down. There are way too many sites euphorically lauding self-employment, but few deal with the huge risks involved, how to deal with them and/or how to avoid them. Certainly, if I’d had this knowledge back when I went freelance, I simply wouldn’t have.

    The most important thing to do is to start freelancing from the security of a job. If it doesen’t get off the ground when you devote 10-20hrs per week to it, you can still always fall back on that, or use it as a financial springboard if it does. Freelancing directly after school or college is the best way to ruin.

  13. it consulting bay area

    Wow, that really is a lot of stuff to be learned from that whole experience. I dont know if i could take a risk like that and just up and leave my job and try to go out on my own public speaking and all of that. That really would be a hard thing to do and I am glad to see that through all of the struggles and hardship you learned something from it all.



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