5-year birthday candleMay 1st was the official 5-year anniversary of launching my consulting firm, User Effect. In the fall of 2005, I quit my job as VP of a 16-person software company (after 8 years). I liked the people and the work was ok, but something just felt wrong.

I can give 100 reasons for why I quit, but only one really matters: when I walked from the car to the office door, I could feel a storm gathering, like one of those rain clouds that follows people in a Peanuts cartoon. I hated my job, and I was tired of pretending that I didn't.

Last year was a big year – I really solidified my direction, doubled my revenue over 2009, finally incorporated and did a lot of i-dotting and t-crossing, all while turning 40 and being a first-time dad. You'll never hear me say that I've "made it" (I'm my own worst critic), but I've learned a lot in the past 5 years, and I thought it would be a good time to share a few of those lessons:

1. You're never the boss.

If there's one thing I'm tired of hearing from people, it's probably: "It must be great to be your own boss." At one point early last year, I counted and realized that I had something like 17 bosses. In other words, 17 different people could call or email me, and I would most likely agree to do what they said (if I wanted to keep them as clients).

Of course, I'm a consultant, so you might think it's different if you're a writer or creative type. Even if you don't have clients, you have an audience, and make no mistake – they're the boss. I write for a 90K-subscriber search marketing blog, and I can tell you that each of those 90,000 people are my boss when I'm working on a post.

You'll always be accountable to someone, and that's probably a good thing.

2. You have to want it.

There are a lot of thankless tasks when you're your own boss. You know how someone at your office sells the projects, picks up the phone, pays the phone bill, changes the toilet paper, makes the coffee, bills the clients, pays the taxes, mows the grass, and makes sure you get paid every 2 weeks? Those "someones" are all you now.

For techie types, the hardest part of that is that you have to sell, and you can't sell if you don't want it. Pick your word: "passionate", "hungry", "motivated" – you'd better be all of those things.

3. Freedom is terrifying.

Some people think that the worst thing in the world is being told what to do and when to do it. Freedom sounds good, until it's staring you in the face. There's something about the void of limitless potential - of knowing that you could do anything today - that can be absolutely horrifying. You'll stare at the computer, paralyzed, and you'll second-guess yourself into a fetal position. Make sure you're ready for the reality of total freedom, and not just the fantasy of it.

4. Look wide, aim narrow.

When you're just getting started, you want to do everything and please everyone. It's normal to not want to turn away any business, but when you aim for everything, you end up with a vague, indecisive message. Worse yet, no one you talk to can really communicate what you do to the next person (in other words: goodbye referrals).

It's tough, but you have to pin yourself down and take aim at something small. When I launched my packaged site audits (usability-focused), it was really tough. I'm a generalist, and I wanted to keep my options open. As soon as I did that, though, people started getting what I was all about. Ironically, even though they didn't usually buy the audit, it got them talking to me and actually broadened the scope of my client work.

It takes good aim to get your foot into a closing door. You've got plenty of time to widen your reach once that door opens.

Stepping away from business, I see this same issue in my broader life (and my friends' lives) as we've hit our 30s (and now 40s). We don't want to make choices, because picking a direction means giving up on some other direction, and that would mean throwing away one or more of our dreams. I think that's the essence of mid-life crisis.

Make no mistake - if you never choose, you're throwing away all of your dreams. At some point, you have to pick a direction – moving North means you can't go South for a while – but your only other option is to stand still.

5. Envy is completely useless.

When you go out on your own, you'll be bombarded by envy. Your friends will envy you for having freedom and being your own boss (see point 1). You'll envy them for having a steady paycheck, health insurance, and a 401K. Once you start working, you'll envy everyone on the internet who's doing everything better than you.

Let me be blunt – all that envy is absolutely fucking useless. Every decision in life has tradeoffs, and some things are going to be harder when you're on your own. If you sit at your desk staring out the window feeling jealous of everyone who walks by, you will fail.

I'd do it again in a heartbeat.

I'm not sure I've painted the brightest picture of self-employment, and there are plenty of tough days, but I'd make the same choice over and over (if the warp core breached and I got stuck in a time loop or something). I've realized over time that I don't work the way people are supposed to work.

Sitting in an office from 9-to-5 (or 8-to-8) is like wearing my skinny jeans because I ran out of laundry – it's uncomfortable, I can't breathe, and my manhood gets squeezed in unfortunate ways (figuratively-speaking).

I love not commuting, I love making lunch in my own kitchen, and I absolutely love spending even a few minutes extra time with my daughter. I'm not saying I'd never go back to an office, but I have no regrets at all about the direction I've chosen.

I can't close this out without thanking a few people, most of all my brilliant, lovely, and hard-working wife, Nancy. I'd also like to thank my old friends and clients at Seminar Information Service and Tews Interactive, as well as the great teams at SEOmoz and Walker Sands with whom I have the good fortune of working. Special thanks, too, to everyone who's read and supported the User Effect blog and my work across the industry over this past 5 years.

10 May – Andrew David Baron

Great article! I've been on my own for 2 years now and it's been an incredible experience. It's definitely NOT for everyone. Some people would NEVER get any work done. Personally, I work better on my own and doing my own thing. Like a true Aquarius that I am...a free spirit to consult to my heart's content.

Pete, really, really great insights here and I would implore anyone who is even THINKING about doing something on their own to FIRST read your article and then have some perspective.

10 May – Dr. Pete

Thanks, Andrew. It was honestly a good 6 months between leaving my job and deciding to go it on my own, and it took a few months after that to really get into the work-at-home groove. You have to find that self-discipline one way or another, or you have to finally run out of things to watch on TiVo :)

10 May – Andrew David Baron

Thank God I don't have a TV, microwave, or extra room for clutter in my life. I'm totally about getting focused and present.

10 May – Alex Angelico

As you say, for me the most difficult part of working by my own is the Look Wide Aim Arrow issue. Now, after almost 4 years I kind of stick with what I'm best at, but every time I let something that COULD BE an opportunity (far from what I'm best at) I feel as "And if this would have been the best opportunity in my life and I let it go?"...
And I also agree with the many bosses, and with the "You have to want it", and with the...

17 May – Ian Miller

Great article, and an awful lot of it even applies to an agency too such as maintaining focus. Just because you can do everything doesn't mean you should.

17 May – Dr. Pete

@Ian - Yeah, a lot of this actually applied when I was helping build up a start-up, too. Working for yourself makes some challenges more intense (and others less), but the fundamental challenges of work-life balance, juggling demands, and finding what you're passionate about are always there, no matter what the setting.

17 May – Deb

Congrats. I need to learn 4 & 5.

17 May – Dr. Pete

@Deb - I find I have to re-learn #5 every single day.

17 May – Sean Hecking

Dr. Pete,

Great post and advice. #4 is probably the most important lesson freelancers/consultants will learn when starting out. You can't be everything to everyone.


17 May – Elle

Excellent article, and you've hit the nail on the head. I've been working my own freelance business for coming on 6 years now and everything you point out above is the absolute truth. I think the one thing you neglected to point out though, is how those friends around us think that, since we run our own business, we have endless freedom to go out and do whatever we want at any time. Ha! I get this all the time. In reality, it can often be more constricting working for yourself - sometimes being required to work late or irregular hours in order to make a deadline, and often letting vacations slip by because we don't get paid for not working. While there are occasions where freedom has it's benefits and we do get a random day off, those days are not often planned or dictated by us, but by the client. On those days I like to hit a nearby golf course, but that's only happened a few times in the last 6 years. I wouldn't change it for the world, but being chained to my desk at home instead of the office is not the freedom many people think it is. :)

17 May – Dr. Pete

@Sean - I struggled with that for 2+ years. I wanted to "keep my options open" which, ironically, meant a lot fewer options.

@Elle - It's funny how work-life balance can get even tougher when you're on your own. The down side of flexibility is that your work and home life just blend into each other, and suddenly you're working all hours of the day. You can theoretically take a vacation any time, but you never do. You have to build it in, eventually.

25 Aug – Website Usability

Lovely article. I liked "Look wide, aim narrow". good for newbies. Thanks for sharing.

02 Sep – Alexander Buck

Great post Dr Pete. It kind of brings it home to me how far I have to go, having just set out on my own in July 2010. I recently read this great quote about mastering the art of living, which I think helps tremendously when thinking about work/life balance......

The person who is a master in the art of living makes little
distinction between their work and their play,
their labor and their leisure, their mind and their body,
their education and their recreation,
their love and their religion.
They hardly know which is which.
They simply pursue their vision of excellence and grace in whatever they do,
leaving others to decide whether they are working or playing.
To them, they are always doing both.

Hope you find it as inspiring as I did, and still do.,

02 Sep – Dr. Pete

Good stuff - thanks, Alexander. It's definitely an ongoing process, at least as long as we're still living.

16 Nov – Mike

I could only hope my online endeavors allow me to be as successful as you. I am a college student preparing for graduation in the Spring, and would like to have some sort of internet business to fall back on through these economic times(I've heard nightmares about the job market in the field my degree applies). Do you have any recommendations on a strong start up?

16 Nov – Dr. Pete

@Mike - I'm afraid there's no easy answer to that one. As a fallback, I probably wouldn't focus on a full-blown start-up in the sense most people think. Build your reputation online, become known as a specialist in an area, and see if there's money to made leveraging your expertise. You can make a good side income (and, eventually, a living) from consulting. People tend to think all-or-none, but there are a lot of ways to make some supplemental income without being the next Steve Jobs.

01 Apr – SEO Sheffield

Nice website. Very cool content. Thank you!!!