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The question

I recently quit my job to pursue my dream of starting my own business. My problem is procrastination. I'm having a hard time maintaining self-motivation without any structure in my days, a boss looking over my shoulder and an office to go to. I am wasting too much time on Facebook, sitting at home in my sweatpants. I'm also not that good with rejection. I'm in a competitive field and so I'm worried if I don't pull myself together, I'm going to lose out to other people doing the same thing. Any suggestions?

The answer

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There certainly is no shortage of ways to procrastinate and waste time. You can almost hear the sucking, vacuuming sound as social media hoover up untold person-hours of what might otherwise have been productive time.

But my own feeling about procrastination – and this is after a lifetime of working mostly on my own – is a little isn't necessarily such a bad thing.

Maybe even necessary. One writer I know says, "My work day begins when I tidy up my office." Agatha Christie said she always got her best ideas while doing dishes. Sometimes it helps to think, get your ducks in a row and/or step away to let the wheels of your subconscious chew over a problem, obstacle or dilemma.

But not for too long. You can't let it become debilitating. You can't get freaked out and start to think, "Well, I wasted this much time, there's no point."

In this regard, I like to quote tennis legend Jimmy Connors: "Do not look upon a period of inactivity as a failure. Rather treat it as a challenge and try to get back on track as soon as you can." In other words, you wasted enough time procrastinating. Don't waste more on regret.

In your case, I suspect, from what you've said, that your paralyzing procrastination might be connected to your fear of rejection. Hey, if you don't really try, you can't fail/be rejected, right?

Here's my trick. Let your fear of what will happen if you don't do your work and get it out there outweigh your fear of rejection. Balance fear and joy. I love writing and wake up every day champing at the bit to get cracking. But I also wake up picturing bailiffs marching my furniture out the front door.

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Other thoughts:

Might be cliché, but it helps to have bulletproof self-belief. And it doesn't hurt if you can surround yourself with people who believe in you. I'm lucky to have a wife and friends who, if I experience reversals or setbacks, say stuff such as, "The universe is unfolding as it should, Dave."s

My children have even gotten in on the act. "Everything is going to work out great for you, Dad. I just know it," they say.

It's good to have heroes – people who have blazed the way on a similar path to the one you're on that you can admire from afar. It's even better if you can find mentors, people who have been successful in your field and can help to guide you from up close.

Oh, and ixnay on the sweatpants. Even though you're home, dress for work. A little trick I learned from my father: In university, he wore a jacket and tie to take tests. Everyone (no doubt) rolled their eyes and thought he was crazy – until he won a scholarship to the Massachusetts Institute of Technology. Yes, that MIT.

(If you do find yourself slipping into slothful ways and sweatpants, here's a surefire cure: run an errand in them. It's an immutable law of freelancing; the worse you're dressed, the more likely you are to run into someone you know.)

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If you work hard, enjoy what you do, surround yourself with supportive friends and mentors and act and dress like you mean business, things are bound to break your way.

Having said all that:

Self-employment and self-motivation are not for everyone. It takes a certain type. Some people need structure, other people around, a dress code and a boss breathing down their neck. If that's you, the sooner you dust off that résumé and elbow your way back into the go-to-office work force, the better.

Are you in a sticky situation? Send your dilemmas to damage@globeandmail.com. Please keep your submissions to 150 words and include a daytime contact number so we can follow up with any queries.

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