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Quit Like an Entrepreneur

You’ve dreamed of this moment. You’ve done the planning, you’ve run your own business on a part-time basis, and you’re convinced it has legs. The concept is proven, the numbers are there. You can go full time. You can go all in. You can make your living on your own, without the 9-to-5 job you’ve been relying on until now.

It’s time to quit.

Leaving your day job is no small thing. It’s one of the most important transitions of your entire life, right up there with puberty and giving up jean shorts. The exit has to be well thought-out and well executed. Your exit strategy has to take some of the pressure off, and set you up to succeed.

Crucially, your departure has to be communicated in a way that leaves bridges unburnt.

I know the feeling. I was a successful, comfortable department head and teacher at a university when I decided to break out into independent business. It was anything but easy to quit, but quitting with an intentional mindset made all the difference.

When you’re finally ready to pull the plug on your 9-to-5, make sure you do the following:


I didn’t quit my job until a year after I decided to.

That’s right, a full calendar year. Part of that was due to the special requirements of a teaching position, which require very advance notice of a resignation. But long before I was contractually required to announce my departure, I was making moves. I was plotting and planning, putting the pieces in place so that I could move seamlessly into my new life.

You really can’t plan your departure soon enough. The more planning you do, the better it will go — even if new factors arise that change some of the details or push the date back. Get every duck you can in a row, now. The fewer gaps you leave, the easier it will be.

Above all, get your revenue projections in order. You might not be able to predict exactly how much money will come in once you’re full-time, but you know how much is already coming in from the current part-time version of your business. Based on that, determine if your business can really replace your income. If it can’t, stay put.

Adjust Your Expenses

Way before you head for the exit, start living lean. Do whatever you have to do to get your personal expenses within the boundaries of your projected revenue.

Start by making a complete budget. Write down every single expense you have, down to the penny, on a spreadsheet. Then, start cutting. To paraphrase Ben Franklin, a penny ruthlessly sliced from your cable bill and sushi budget is a penny added to your overall profit.

Don’t be afraid to go big. Despite all the bootstrapping lectures from personal finance bloggers, giving up your morning coffee won’t be enough to balance your books. Move to a smaller home, or one in a less expensive area. Cut the major expenses, and let the size of your sacrifice reflect your commitment to your independence.

When I left my job, I made two huge cuts: I sold my car, and relocated to a city with solid public transportation. With no car payment or insurance to worry about, and a stripped-down lifestyle that included very little by way of new clothes and dinners out, I was well in the black every month.


Preparing to be an entrepreneur means getting your time management game on point. The worst thing you can do is wake up on your first day post-conventional-job and not know what you’re supposed to do, or when. A consistent, planned schedule will keep you in a productive mindset when there’s no longer a clock to punch.

Take the time to sit down and work out what schedule will work best for you. Build your ideal schedule around the personal things that matter most, including time for working out, relaxing, socializing, and (don’t forget this one) sleeping enough. Now that you have the freedom to dictate your own schedule, do it with intent.

Not having a schedule — or not sticking to it — will eventually derail you. Do not let the freedom of entrepreneurship be your downfall. Decide when your working hours are, and during those hours, work without distraction of any kind.

Break the News

Let me be clear: there is no advantage to pissing off your employer on the way out. Your last act as a conventional employee should be to exit gracefully, and leave as a respected, valued person who’d be welcomed back in a heartbeat.

Obviously, that means taking some responsibility for easing your employer’s transition. Give as much advance notice as you can — nothing less than 2 or 3 months —- and offer to train your replacement.

Don’t sneak out the back door. Request a face-to-face meeting and break the news in person. It might be awkward. It might even be extremely unpleasant. But if you can’t navigate awkward, unpleasant interpersonal business matters, you’re not cut out for running your own company. Best to get your practice in now.

Explain that you want a challenge, that you have a passion to see how far you can go on your own. Express genuine gratitude for whatever you got from the job, even if it was just a means to keep a roof over your head. Be as impressive in your exit interview as you were in your hiring interview.

Be nice, even if your boss was a jerk and you can’t wait to get the hell out of there.

Most importantly, take the opportunity to get some feedback. Ask your employer what they think your strengths and weaknesses are. Encourage them to be honest and open, and get a valuable picture of yourself from someone else’s perspective. Take that information seriously, and use it to make yourself a better entrepreneur.

As you come to the end of your time, don’t coast. Finish strong, and do the kind of great work that will make you missed. Leave knowing you did a great job right up to the last minute, and let that momentum carry over into your new work.

When I quit my job, it was not an easy conversation to have. It was hard to put a positive spin on what is, professionally speaking, a non-mutual breakup. That’s why I did the only thing any of us can do when we’re announcing a major change: I reached for honesty. I simply told the truth as someone who was undeniably called to something new, and couldn’t possibly be fulfilled if I stayed in one place, unable to grow or change.

Each of us has the right to make the most of ourselves, even by taking a huge risk. Any decent employer can respect that, and won’t hold it against you. If your employer can’t see it that way…you know where the door is.