Sincerely, Sara: Do I Risk My Corporate Job To Run The Start-Up of my Dreams?

Hi Sara,

I’m doing well in a career I’m good at, but I’m not passionate about. If I continue on the same trajectory with my current company I’ll be making over six figures soon. I have excellent benefits, in a financially strong, Fortune 500 company. This was all great until I recently got an offer to work with a small, brilliant team launching an innovative company that would pretty much be my dream job. If I take the leap, I’ll be excited to be at work every day. But gone is my stability and great benefits, and even though I’ll have the opportunity to make more money than I ever dreamed of making in my current career. It will mean a period of sacrifice until the revenue starts rolling. And if we don’t get the company off the ground, I’m back to square one: no stable but boring job and no job working with a cool team I’d hang with even on my days off.

I’m the type of guy that’s always wanted to run with the bulls in Pamplona, or bungee of a huge bridge, but I’m not sure I could ever go through with something that puts my future at risk.


Wants to Run with the Bulls, but Afraid of Getting Trampled

Dear Wants to Run,

Your quandary forces you to choose a side: passion or paycheck. Many of my entrepreneur friends  have left well-paying  corporate gigs for jobs that serve a social good they are passionate about, but is not financially lucrative,  and have made the same leap of faith to follow their bliss.  Even when their decisions have come at the expense of a comforting retirement nest egg and a killer medical plan, the sense of security they sacrificed didn’t compare to the joy and purpose of doing something with their lives that meant more to them than anything they could deposit into a bank account. Some of them are impacting communities, changing lives and transforming the world.

What price do you put on purpose and happiness? What is the freedom that comes with making your own way in the world, on your own terms, worth?  Here’s the rub: We live in world where our necessities must be paid for in order for us to survive, but how do we compare financial compensation with something that we can’t calculate in monetary terms?

I realize that I’ve asked more questions instead of offering an answer, but I still need to ask one more. Are you relying on your paycheck and benefits to provide for a family? If there are people that depend on your steady financial situation for their livelihood than your dilemma becomes decidedly more complicated. You will need to figure out if you have enough savings to cover your expenses until the new company is generating enough profit to provide for all of your needs. Keep in mind, it may take years for a new business to fine tune a workable business model, and can go through financially painful growing pains while they adapt to the market. Assess what options you will have for securing another well-paying position if your start-up fails (which many do). If you are free of familial obligations, then perhaps it’s an ideal time in your life to chase an opportunity like the one that just landed in your lap. If not now, then when? Certainly the time isn’t once you have the responsibility and expense of children. 

You will have to live with this decision every day, at least 8 hours a day, 5 days a week, for weeks, then months, and then years. Do some soul searching and discover what is really what you want out of more than just your job, but out of your future—and your life. Then compare the two paths. Which will bring you closest to your end goal?

I would also advise you to consider that: 1. The best laid plans do not always pan out 2. If anything has proven that “security” with a “stable” company can be more of an illusion than we once believed it to be, it’s the recent financial crisis that bankrupted companies like AIG,  Bear Stearns, and Goldman Sachs and cost many loyal employees from formerly financially robust companies to lose their hard won pensions and drained their 401K packages. And I’ll offer one last one point for your consideration, “Life is what happens when we’re busy making plans”.

So what do you want your days to be like? That’s the real question. Are weekends entertaining in a big house, or summers vacationing in the Keys, the moments you live for? Do creating original solutions that change the way people interact invigorate you with joy? Does the freedom to engage in work that challenges and satisfies you mean more than a second car or a vacation home? If what you really want is a life bursting with new, exhilarating experiences that remind you how thrilling it is to be alive, you can create it. But you will have to be prepared to make the sacrifices necessary to bring that life into existence. Your time and happiness are the most valuable things you own, so guard them with your life.