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When your dream job becomes a nightmare, don't be afraid to start over

For this sales trainer, walking away from the company he loved was the best thing he did for his career.
Image: Two men work in an office
It’s good to love your work, and to believe in it. But it’s unhealthy to let your job define you.svetikd / Getty Images

Have you ever dreamed of getting in on the ground floor of a startup that ultimately gets sold to a multi-billion-dollar company? I did. Then after it happened, I ended up sobbing in a parking lot — and not tears of joy. It was a painful, difficult time.

But I ended up with a whole new career and much better, happier life — not just for me, but also for my wife and daughter.

It’s a story no one tells you. Glamorous images of young, scrappy workers becoming overnight millionaires, or billionaires, have become a part of the national and even global consciousness. The idea that an acquisition can have a serious downside — for you personally and for the startup you’ve helped create — rarely gets any attention.

Having come through that dark period, I now know the steps anyone can take to avoid the pitfalls.

See the signs

I was the fifth employee of a Boston-based startup. Our three founders made me their second hire. We grew the company to a staff of 85. What I loved most about it was the sense of teamwork — a necessity for today’s businesses to succeed. Collaboration increases innovation, speed, creativity and more. Most importantly, it makes you want to come to work each day and give it your all.

But when a household name company wanted to acquire us, that spirit of our business suddenly went out the window.

Now, our founders were holding meetings behind closed doors, keeping us out of the loop. They instructed us to improve our numbers by working to the bone, drastically cutting back on expenses — and pretend that operating at that level would be sustainable for the long term. Our engineers were even told to bring in their personal laptops because the business wouldn’t buy them new, functional ones to replace the aging ones at work.

It came down to money. Our founders stood to make millions from the sale, while the rest of us would make a lot less. We were fine with that, but wanted to keep the sense of teamwork.

I refused to see it at the time, because I loved our startup. But that was the beginning of the end. When your business gives up the culture that makes workers engaged and satisfied, it gives up what’s made it successful.

When you see this happening, there’s a good chance misery is in store. It’s time to start looking for work elsewhere.

Trust your instincts

I’m generally pretty blunt. My colleagues and bosses can count on me to tell them the truth. And that has served me well. So when my boss instructed me to be dishonest, I should have refused.

He told me that the point person at the big corporation wanted to meet with me to discuss sales. I had to pretend everything was just great, and not let on that we were working at an unsustainable level. The deceit made me uncomfortable — and the point person sensed it. He later told my founders that he didn’t have a good feeling about me.

I should have been honest. Months afterward, when I had left the company, I met again with the point person at the corporation. He said I should have told him everything. “What would have been the risk? There are two possible outcomes. The first is that I would be open to your approach, we would make a connection, see eye to eye and ultimately have a healthy relationship moving forward. Win-win for everyone. The second is I would ream you out, tell (your boss) you went over his head and destroy your relationship with him and me. Let me ask you something. If that had happened would you have wanted to work for me?”

My answer was an obvious no. “Then,” he said, “you would have found out very early on in this relationship that this was not the right job for you and would have been able to make the appropriate decisions.” He was right.

Don’t let your work define you

It’s good to love your work, and to believe in it. But it’s unhealthy to let your job define you.

That was my biggest mistake. Though things continued going badly with the acquisition, I was afraid to leave the job. But when I was demoted (another way for them to fire me), I felt crushed. On the way home, I could barely see as my eyes welled up with tears. I pulled over into a grocery store parking lot and lost it. I called friends and my wife, who talked me through it.

Embracing a new beginning

In the end, it worked out beautifully for me. I decided to leave, opened my mind to new career possibilities, and was given a chance to join a different company as a sales trainer. It was exciting and invigorating.

Today, I’m happier than ever running my own company. It took some time to ramp up business, but I’ve gotten to set my schedule, be my own boss and share my experiences with clients. I also guide corporations toward empowering their sales staff and creating team sensibilities so that they can all experience what I had at my startup. I feel happy and fulfilled. In our family, we have time for each other. And our daughter is growing up seeing both mommy and daddy feel great about their careers.

No matter what field you’re in, there’s a good chance you’ll run into similar challenges. Remain true to yourself, and don’t be afraid of change. It can pay off in ways you never imagined.

John Barrows is a sales trainer for leading companies. He blogs, including about this experience, at


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