Risk Now or Forever Hold Your Peace

The older we get, the more permanent our decisions become.

In high school, the biggest decision we made was probably what school to take (a lot of people I know didn’t have a choice in this matter as well), or perhaps what course to take.

We could then easily shift courses. A lot of people I know even shifted schools.

We also choose who to hang out with. This can change easily as well.

Then one day, we graduate from college.

Then we have to face the next big decision in our lives – what job to take.

Not quite happy with our first job, perhaps we transfer to another firm. It isn’t as easy as changing courses, but this decision is still flexible enough that for a lot of us, we do this several times in our first few years out in the corporate jungle.

By this time, perhaps our relationships deepen as well. Soon enough, we start getting invitations for weddings. One day, we ourselves get married. We often hear of a lot of stories of people getting “cold feet.” This is natural. This decision is permanent, so we take our time. We get anxious.

Meanwhile, our jobs take some sort of pattern. The sum total of our jobs and our experiences becomes our “career.” This is an over-arching decision that is difficult to undo. If we’ve taken on a “marketing” career, then we would think long and hard before deciding to become a programmer. The longer the career, the more difficult a potential career shift becomes. The more the investment, the more difficult it is to let go.

If at one point we realize the career path we’ve taken isn’t quite what fulfills us, this can lead to many a term-crisis.

Then we start having kids.

You’ve heard how this can change everything.

This changes everything.

Suddenly, you literally aren’t living for yourself any longer. Suddenly you’re thinking – I want to send them to good schools! But where will I get the money for tuition? I want to get them HMO coverage! What will happen if I kick the bucket? O gosh, does this mean I have to talk to that pesky life insurance guy? Where will I get the money for insurance payments? Who picks them up from school?! 

It’s a crazy, never-ending cycle of worry and planning and spending.

It’s also extremely fulfilling and a source of profound joy 🙂

At this point however, it’s extremely difficult to carry any form of risk.

Recently, I’ve been talking to a very accomplished friend of mine who’s just above 40. He’s contemplating the jump to entrepreneurship. Our lunches have gone on for about a year now.

In one of our lunches, I asked him, how much will it take to get you to make the leap? How much are your expenses?

With potential startup founders, the salary question isn’t “how much do you want?” but “what’s the least amount you can live with?”

The answer almost made me jump out of my chair.

I know he’s reading this – yeah dude, I almost fell off my chair – but my vast composure powers prevented me from flinching.

I told him, “No startup can accommodate that.” He nodded in slow approval.

In our subsequent talks, this amount became the sum we have in our minds for him to consider a jump. Financially at least, the distance he has to leap has become a Grand Canyon. Whatever startup he cooks up has to pay this amount.

We both acknowledge, however, that this isn’t even the biggest hurdle.

One lunch I was lamenting to him about this other person who was about to take the leap, but didn’t.

He told me:

“You have to give people our age some slack. We don’t think that way.”

I realized he was right. After 15-20 years of corporate, it’s just hard for people to re-imagine a career outside corporate. Even if the desire was there. 

In one of my earlier posts, I noted how a great number of the people I interviewed over the last nearly 20 years I’ve been in HR said “I want to create my own business,” when asked what their long-term plan was.

This just doesn’t happen often. The older we get, the lesser our ability to risk becomes.

Yes, some people get to invest in startups when they get older. But this isn’t a function of getting older. It’s a function of financial success and generating enough money to consider angel investing.The rule of thumb is that as an angel, you invest only 10% of your disposable income. (translation: by-the-book angel investors don’t really risk) Interestingly, a vast majority of angel investors I’ve encountered are ALSO entrepreneurs. Truthfully, I haven’t met anyone who’s a corporate lifer who’s now into angel investing. A number of older corporate folks leverage on experience and go the consulting route. But this route often lacks the ambition and scale of what a modern startup wants to do.  (translation: long corporate careers do not lead to startups)

My advice?

If you are under 35, have no kids yet, and you possess the entrepreneurial fire in the belly. Don’t wait. That fire has a shelf life.

Leap.