Making the Switch from Startup to Corporate Mid-Career

You’ll find plenty of advice online about transitioning from a corporate job to a startup gig. After all, making it big at the next Facebook or Uber is the new American dream. Who among us hasn’t imagined late nights around the table tennis table, with the promise of untold wealth following an initial public offering? The reality is, however, that most startups don’t make it to the initial public offering (IPO), and you might find yourself burnt out from long hours mostly spent on your laptop. It’s OK if you find yourself longing to return to a big established company. You just need to know the secret to successfully transitioning back: understanding what to expect from the corporate world.

Consider the pros and cons of startup vs. corporate

Before you start applying for every corporate job you come across, make a list of plusses and minuses. Ask yourself the following questions so you go in with eyes wide open:

• Are you tired of juggling multiple roles at your startup? In a large corporation with more people to share the work, you will likely have defined responsibilities as part of the bigger team. Pros to corporate: more certainty, less chance of consistent long hours. Cons: fewer opportunities to take on new challenges.
• Are you frustrated by your startup’s uncertain pay and benefits? That’s the tradeoff for potential stock options down the line. In a corporate gig, paychecks, health insurance benefits, etc., are a surer thing—but the chances of a financial windfall are slim to none. How much financial risk can you tolerate in your current stage of life?
• Are you exhausted by making it up as you go along? To use a common metaphor, you’re typically “flying the plane as you build it”—often with limited resources. In the corporate world, you will generally walk into established processes and budgets. Which scenario sounds most appealing to you?
• How much do you want to influence company culture? At a startup, you likely know the CEO on a first-name basis, and you may have a seat at the table when it comes to determining company culture. In a large corporation, that culture will be well established—and, let’s be real here, some aspects of it, such as corporate speak, may be eyeroll-inducing. But the allure of some startup benefits (craft beer on tap in the breakroom) can wear thin when your kid needs braces.
• How much flexibility do you want, and in what areas of life is it most important? Startups are known for having flexible environments. After all, no one has had time to write an extensive employee policy manual, and there aren’t enough employees to necessitate much in the way of red tape. The tradeoff for lack of structure is an always-on mentality. Sure, you might have unlimited PTO, but you’ll be expected to take calls and monitor your email from that beach in Hawaii. The corporate world might contain several layers of bureaucracy and limited vacation days, but you’re more likely to get a true break when you do take PTO. What style of flexibility is most important to you? Would you rather keep a more routine schedule with the promise of uninterrupted nights and weekends?

If you make your list and find the list of minuses is longer on the startup side, then you’re ready to make the leap back to corporate. Keep in mind your preferences may change as your lifestyle changes. Your relationship with work can shift depending on whether you have a spouse or partner, children, or aging parents.

Staying happy once you’ve made the switch

Once you’ve landed your new corporate job, hold on to your pros and cons list. The day may come when you find yourself longing to bend the CEO’s ear with your latest innovative idea—except the CEO is several rungs up the ladder and reaching out would be a major faux pas. If bureaucracy and procedure start to get to you, pull out your list, and remember the long hours and uncertainty that propelled you back to the job market.

And remember: Nobody’s perfect. And no job is, either.