It’s been five full years since quitting my full time job to go after my long-time dream of traveling and writing books. It’s been a crazy, wild, totally unexpected, sometimes heartbreaking, other times completely exhilarating, ride.

I’ve learned more about myself and about what it takes to achieve success in the past five years than I have in the rest of my life combined.

People ask me, “do you ever regret quitting your job?” The short answer to that question is no.

The long answer goes something like this.

Quitting your job won’t solve your problems

There were a lot of things I hated about having a full time job and I was convinced getting rid of the job would solve them. I hated the scheduling conflicts, the office politics, the bureaucracy, the overwhelming wave of insecurity I would feel under observation.

I hated evaluations. 


I hated what felt like my boss “breathing down my neck”.

I hated not having the flexibility to take a day off when I needed—or spontaneously, because after long winter, it was finally sunny outside.

Here’s the thing. There are a lot of perks to working for yourself. The spontaneity thing, first of all. The freedom to make your own choices. That rocks. But quitting my job did not make me feel less insecure. It didn’t solve all my scheduling conflicts.

Nope, that’s just me—expecting too much of myself, thinking I could do more than I actually can.

Quitting your job does not solve all of your problems. Our problems have this strange habit of following us.

There’s no such thing as a “perfect” work environment

There are some good work environments and some bad ones. I quit a job once because my boss would yell at us—the entire team—on a daily basis. Pretty sure he thought it was motivating. I just thought it was unprofessional and unhelpful. So I quit.

But even the most wonderful work environments are not perfect.

Work environments reflect the people inside them—endearing and imperfect as they are; and truly great work environments are fought for and won. They’re built with hard work and honesty, over a long period of time.

Even when I have total control over my work environment, it’s still not perfect because I’m not perfect. It’s a little manic at times, like I am. And although it typically is conducive to creativity, it runs on stress and caffeine.

The workplace I create is a reflection of me and it’s amazing how even the people I invite into that space get wrapped up in the tornado of my gifts and problems.

No workplace is perfect.

If your workplace is awful, quit.

If it’s average or above average, ask yourself what you can do to contribute to the work environment and make it the kind of place you want to be.

We must abandon the mythology of “total freedom” in our work.

I couldn’t wait to quit my job so I would have “total freedom” to work when I wanted to work, to write whatever I wanted to write, to change plans at the last minute and to take a day off whenever I felt like I needed it.

Let me tell you, after five years of working for myself, there is no such thing as “total freedom” in your work. At least not as far as I’ve found.

[If you have discovered this secret, please email me. I pay cash money.]

The search for the elusive “total freedom” in my work has led me on more than one wild goose chase and has probably prevented me from making the progress I really desire. You’ve heard the old adage, “creativity needs boundaries”. I’d say that applies pretty well here.

The trick is finding the right boundaries so your creative energy can flow and you can thrive.

Someone has to be the boss.

I was so excited to quit my job so I could duck out form under the weight of my the dreaded “boss”. From my artistic position, even the best bosses were stifling my creative energy and preventing me from achieving my goals.

But here’s the deal. Someone has to be the boss.

Someone has to make sure the company is being productive, that money is coming in, that systems are in place to keep everyone on track, that everyone is doing what they’re supposed to do based on those systems and that everyone is given permission to succeed and grow.

Someone has to be the boss.

The boss has to be concerned about wasted time and energy and about the bottom line because, ultimately, he or she is concerned about making sure everyone leaves at the end of the week with a paycheck.

Even when you work for yourself, there’s no escaping “the boss”.

The boss just might be you.

Every creative person wishes they didn’t have a boss. This is impossible. Instead, ask yourself who you want your boss to be.

I was an ungrateful and selfish employee.

I was such an ungrateful and selfish employee, taking things for granted that were huge blessings to me—like bonuses, paid days off, a 401k, a steady, regular, consistent paycheck, unending access to office supplies.

I took too many breaks and didn’t maximize my productivity like I know now I could have. I didn’t see how my actions (or inactions) impacted the company or organization as a whole.

Now that I run my own business I see it and feel it.

I feel the price of every box of pens, of every time I have to buy toner. I feel every hour I take off and every day I don’t work. If I don’t do something, it doesn’t get done.

So I see very clearly how my actions impact the organization’s bottom line, which in the end, impacts me.

So these days, I treasure every long lunch, every day off, every printed piece of paper, and every day I’m lucky enough to call this my job.