The Big Break

Your hot startup was bought by MegaCorp and after 18 months of mind-numbing meetings to integrate the companies your new, new, new boss drops by with the HR director to suggest you may want to move on. It’s time for a big break.

Doesn’t matter how it happens. The chances are very good that if you join a startup, you will eventually be out of a job. The company may have an exit (good, bad, weird, etc.), or you may decide to make a personal exit because you find a more interesting opportunity or simply decided it’s time for something completely different.

So every professional building a career in the world of startups should be thinking about how they handle the big breaks. Turns out most of the work happens before you leave.

Here are 4 rules of thumb to keep in mind:

1. Make it Memorable
After 250 eighty hour weeks, it’s time to do something different. But I see too many executives who are surprised to find themselves unemployed (commonly referred to as “consulting”). Remember, you’re in a startup, becoming suddenly unemployed should not be a surprise.

These stunned Type-A workaholics quickly pepper their days with networking meetings, busy themselves with long neglected household projects, and generally churn through the hours with lots of stuff that amounts to nothing. Weeks that would have been precious during the startup’s heyday burn away like a cheap cigar.

Don’t make that mistake.

The first thing you should do when you are bestowed with a big break is something amazing. Do something you’ve always dreamed of doing — something that will create a memory for a lifetime. Start that arts center in central Sudan; see the pyramids in Egypt; do a photo tour through Southern China; write a screenplay; spend a month building a log cabin with your dad; take your daughter to the Australian outback.

Do not schedule any meetings with interested entrepreneurs, recruiters, VC’s, etc. Just stick your iPhone in a drawer, pack your bags, and go. These are rare moments, don’t miss them. If you pause for a second on your way out the door, you’ll get sucked right back into the next project.

The key to this is to plan ahead. Memorable breaks don’t get thrown together in a few days. So make it a little project you work on to plan that amazing trip, or charity work, or book, or whatever it’s going to be you’ll do when you are suddenly blessed with a few months of free time. Then seize the moment when they turn off your email account.

2. Build Relationships before the Break
While you’re working is the best time to be building relationships. Networking events for the unemployed are a waste of time. Every project you have at your current job is an opportunity to establish new relationships — with colleagues, partners, investors, board members, customers, etc. — that extend beyond that project.

The tendency is to leave these people in the bucket where you first found them, but that’s a mistake. The biz dev director you’re doing a deal with might be the VP of product marketing at your next gig. That sharp investor on your board might be the partner that invites you to be an entrepreneur in residence. The geeky engineer in the cube down the hall might be cooking up an amazing new startup. The recruiter you hired to fill positions today could be placing you tomorrow.

So take advantage of being employed and in the game to develop relationships that will help you set up the next game. Take the time to stay in touch with contacts you make. Reach beyond the moment or task at hand to make more lasting connections. Real professional networks are built when people work together, not standing around awkwardly drinking crappy white wine out of a plastic cup in a beige hotel atrium.

3. Plan Financially
If you’re lucky, as in lottery lucky, your startup will have an amazing payout and your next job will be at the foundation you set up to protect rare and endangered Brazilian tree frogs. But, just in case, save some dough for the big break. Cash in the bank gives you the freedom to be selective.

4. Be a Venture Capitalist with Your Career
Startups are high risk. Whether it’s a new restaurant or a new SaaS application, odds are the company will fail. VCs manage this risk in a number of ways. The default investment thesis is no. They’re very focused on big markets, great teams, and breakthrough innovations. Finally, they diversify their risks across multiple investments.

You should do the same. You have a limited number of years in your career, so you need to invest them carefully. Since entrepreneurs and startup executives don’t have the luxury of investing their time into more than one startup at any given moment, they need to diversify their risk over time.

One way to think about this is to look at your average annual earnings for your entire career. Some years will be good (think liquidity). Some will be bad. In the end, you should see an earnings achievement over the 20 years you spend in startups that at least matches what you could make working at a large established company with a big cushy salary. (Of course, I hope you do much better.)

So as you evaluate what you’ll do next you, be an investor and pick carefully.

Final thoughts
If you plan for the big breaks, they will enrich your life and build your career.

I treat them as a job perk. I’ve taken the opportunity to do the grand tour in Italy, backpack through Southeast Asia, live in a Buddhist monastery, and a bunch of other things that would never fit into a vacation.

Have fun with yours.


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