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A few years ago, a close friend of mine was struggling with his job.  He worked in a large corporation he couldn’t stand:  unethical business practices, employee backstabbing, and sexual harassment all seemed to occur on a regular basis.  He wanted out.  Not only that, for years he’d harbored a secret dream of starting his own business.  Driven by his growing disgust with his company’s culture, he made a determination to do just that.

Every Monday on his way into work he’d daydream about leaving.  But by the time he’d reach his office he’d have concluded that the time wasn’t right.  He had six more months left to pay off a car loan and was planning to get married in nine.  He was well aware of the lean period that most new businesses endure at their start and was worried he wouldn’t be able to weather it.  And what if his new business failed?  Or succeeded, but not at the level he found satisfying or that could sustain his life (and his soon-to-be family’s)?  Wouldn’t it be better to save up a little more money, he asked me one day, to create a bigger buffer for the lean period he knew would be coming, and then make the leap?

“No,” I told him flatly.

Sure, I agreed, having that extra cash would be helpful—but how certain was he that he would need it?

He shrugged uncertainly.

I told him I thought his idea about needing to save more money before leaving was just an excuse to stay where he was.  Yes, leaving his current job and starting a new business represented a risk, a risk he could perhaps ameliorate a little with more money.  But could he eliminate the risk entirely?

“No,” he admitted.

The future is mostly unpredictable, I argued.  We may think we know how things will go, but things rarely turn out exactly as we predict (and often not even close).  He could save up that extra money, buying a feeling of confidence in his choice to leave, and then have a car accident that required him to pour all his extra savings into repairs and medical bills.  Or, I suggested, his fiance, who had a job she loved, could get a promotion and a pay raise and instantly make that extra money he saved irrelevant.

There’s almost never a perfect time to do anything, I told him.  Not to leave a job and start a new business, not to get married, not to have a baby.  If you wait for the right moment to appear, no moment will ever appear to be right.  We do all those things because we want to do them; we do them in spite of all the obstacles and reasons not to.  And when we don’t do them, the reasons we give are mostly designed to disguise the truth that we’re either genuinely ambivalent about doing them or we’re afraid.

This isn’t to say that careful forethought and planning aren’t important.  I’m not arguing here for waking up one day, walking into work, announcing you’re leaving, and waking up the next day without a plan about what to do next.  But my friend had his plan—a thoroughly researched, executable plan.  One that had risks (because the future isn’t completely predictable), but one he thought he could pull off.  One he wanted to pull off.  He’d rationalized his hesitation by telling himself that certain obstacles needed to be removed before he could quit.

“But once those obstacles are gone,” I argued, “other ones will appear to take their place.”  No glowing sign will ever descend from the heavens with an arrow pointing at a day your life will become easy enough to make it the right day to leap.

He agreed with me, he said.  He was ready.  He would do it.

When I caught up with him again a week later, however, he still hadn’t announced he was quitting.

“This is harder than I thought,” he said.

“Thursday,” I replied.

His expression became panic-stricken.  “What…?”

“You’re quitting on Thursday.”

“Are you sure?” he asked.

What I told him was that I was sure he wanted to quit, that he had just as much chance of succeeding as one could have, and that if he never did it, he’d regret not trying for the rest of his life.  I was a close enough friend that I felt not only comfortable but obligated to provide the slight push he needed.  “I believe you’ll be happy if you do this.  Even if, in the end, you fail.”

Sure enough, that Thursday, shaking, sweating, scared out of his mind, he told his boss he was leaving.  When his boss tried to convince him to stay, good-naturedly warning him about the likelihood of failure, a curious thing happened:  his resolve to leave and try his plan hardened like quick-drying cement.

“I’m still scared out of my mind,” he confessed later, “but I’m so happy.”

Within a year, he’d built a small, moderately successful company.  It took him even longer than he’d estimated to start turning a profit, and it ended up being far harder than he’d ever imagined.  It took him two years instead of six months to pay off his car loan, and his wedding ended up being quite a bit smaller than his fiance had originally envisioned.  But she didn’t mind.  “She likes how excited I am to go to work every morning,” he told me.

In the end, he realized he’d been asking himself the wrong question all along. If not now, when? He shook his head.  “That wasn’t the issue at all,” he said.

“What was the issue?” I asked him.

“If not me, who?” he replied.

Next Week: Stupid Fights