Sincerely, Sara: Do I Risk my Comfortable, Boring Corporate Job to Run the Start-Up of my Dreams?

Sara GabriellaBy Sara Gabriella

Las Vegas Informer

Hello 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 while we get things going and 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 doing something that uses skills I’ll never get to use at the job I have now.

I’m the type of guy that’s always wanted to run with the bulls in Pamplona or bungee off a huge bridge, but I’m not sure I could ever go through with taking a major risk like this because I like feeling in control and secure about my future.


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

New LifeDear Wants to Run,

Your quandary forces you to choose a side: passion or paycheck. Many of my entrepreneur friends  and those who have left well-paying  corporate gigs for jobs that serve a social good they are passionate about, but is not financially lucrative, have made the same leap of faith to follow their bliss and live their dreams.  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 overwhelming joy of doing something with their lives that meant more to them than anything they could deposit into a bank account. Some of them were impacting communities, changing lives and transforming the world.

What prices do put on peace of mind, purpose and happiness? What is the freedom that comes with making your own way in the world, on your own terms, worth?  There’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 just 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, and each other. Then 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 a spouse and 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 important to you and what you want out of more than just your job, but out of your future—and your life. Then compare the two paths, cautious corporate path or challenging, but rewarding, entrepreneurial route. Which one 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? Is creating original solutions that change the way people interact or improving the way communities are built, 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? Take a hard look at those questions and the answer will reveal itself. 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.



Sara Gabriella

Sara is a published writer, marketing professional and TV Host. Her writing career has taken her from corporate copywriting in San Francisco to creating content for top network TV shows in Los Angeles, and finally to online and print media in Las Vegas. Her current columns include a media column “Sara in the City” and her advice column “Sincerely, Sara.”

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2 Responses to Sincerely, Sara: Do I Risk my Comfortable, Boring Corporate Job to Run the Start-Up of my Dreams?

  1. I have been a freelance Art Director/Designer for almost all of my career. Many of my best friends had “secure” jobs at large corporate ad agencies.

    One afternoon I was having lunch with one of my big-agency friends, George, and he was complaining how much he hated his job. I told him “If you hate it so much, why don’t you try freelancing”? He looked at me as though I was out of my mind. He couldn’t quit a job that provided so much “stability and great benefits.” Besides, he went on, “They need me. If they lost most of their big-money accounts, I would be the last to go.”

    Early the next week I ran into a mutual friend and the first words out of his mouth were, you guessed it, “Did you hear about George? They let him go.”

    There is no such thing as security. Go with your heart and take n the challenge of the start-up. If the start-up doesn’t work out, what’s the worst thing that can happen? You will have gained invaluable experience and added breadth of your resume.

    Good Luck!

    • Thanks, Jim! That is a more and more common story these days.
      I have sacrificed paycheck for passion many times in my career. It’s always “paid” off, whether with experience, new skills or the type of fulfillment and bliss that only comes from living your purpose.

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