A recent article in the Wall Street Journal suggests that folks who launch companies in their 30s, 40s or even 50s have significant advantages, including experience, access to capital, employed spouses, lack of debt, and so on.

In fact the article stated that, "midcareer entrepreneurs [are] five times more likely to have a going concern five years later than those starting a business right out of college."

When I was an undergrad and thinking of dropping out of school to start a business, I went to my Uncle Todd for guidance. He was the only person I trusted to understand my situation and offer thorough, reliable feedback.

Todd wasn't an entrepreneur; he played for the Oakland Raiders. But he'd won a couple Super Bowls, and this accomplishment alone gave him sagacity and savvy in my eyes. He was killing it--why wouldn't his counsel be golden?

Luckily, it was. I was young enough to gamble without worrying that failure would ruin me, he said. This opportunity would never come again. In short, he told me to go for it. I'm grateful he did.

Today I'm 42, with six girls at home, a comfortable lifestyle and limited energy reserves. I've often wondered how my uncle would have reacted had I approached him at this stage.

A practical man, he probably would have encouraged a little soul-searching on my part. If you're getting on in years, have steady employment, fulfilling relationships, yet find yourself itching to call the shots, allow me to be your very own--admittedly less athletic--uncle and offer the same advice.

Before you dive in, ask yourself the following questions:

1. Are you risk-loving or risk-averse?  

By middle age, most of us have a lot to lose. We've spent much of our lives building our careers, friendships and families. We've saved for a rainy day and enjoy solid benefits packages. We've got car payments and mortgages and kids with visions of elite colleges dancing in their heads.

This is an admirable picture of one kind of success. Countless people would kill for it. And yet you wonder--what if you're selling yourself short? What if there are new mountains to conquer, opportunities to explore?

As compelling as these questions are, they're not critical. What's critical is whether you're willing to risk your hard-won stability in pursuit of the answers. Are you ready, financially, to tighten your belt and take a step back in the hope of future progress?

2. Is your family on board?

I was a newlywed when I quit college. My wife Rachel and I were green, naive and broke. It was easy for her to say, "OK, let's do this," because we literally had nothing to lose.

Imagine me proposing a similar scenario today. "Lover, what do you say we roll the dice on two decades of systematic growth and prosperity on the off chance that my cool but untested idea will pan out?"

I can imagine her response, which would include a gentle but firm reminder that we're the guardians of a galaxy of energetic females, each of whom have big plans. Introducing a radical change now would trigger one hell of a roller coaster ride.

It's possible, of course, that Rachel and I would end up deciding it was worth it. But I'd have to be positive that the people who surround and support me have my back and trust me to have theirs.

3. How much do you really want it?

I recall something my dad told me when he turned 60. He'd owned a succession of businesses, and I was curious about what he planned next.

He said, "Levi, I simply want to coast. I don't have the desire to begin something new. I just don't have it in me anymore."

By "it" he meant a quality that I like to think of as fire in the gut. Whippersnappers have it in abundance--an inferno of ambition and stamina that launches them in all sorts of crazy, potentially lucrative directions.   

It's easy, when you're older, to confuse memories of fire in the gut with the fire itself. You're in some office gig that you hate, for example. Daydreams of startup glory are infinitely sexier.  

But wait. The steady paycheck that means piano lessons for your kids and tropical vacations for you can also create overconfidence. You're doing well within corporate confines, so why shouldn't you do twice as well unrestricted and free?

This is a fallacy. The confines themselves may be the secret of your success. Before you strike out on your lonesome, take an honest inventory. Decide whether your restlessness is a result of fire in the gut--or fantasy. If it's the latter, stick with your day job.

Published on: Nov 7, 2018
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