Smart Lemming Diary: Knowing when to resign from your dream job


Does telecommuting work for executives? When should you resign from your dream job? If you’re unable to perform your job, failing to meet your own expectations, should you exit?

Below is the last journal entry from when I was a VP of Sale Operations and Marketing, resigning from my dream job.

November 8, 2006

I thought that I could manage commuting between Seattle and Manhattan, but it’s not working out as I expected. For the month of October, I struggled to stay connected the Executive team. We had meetings via conference calls, where I could barely hear them over the phone. It was frustrating for me as I’m sure it was for the rest of the team.

After thinking about it for the past month on my daily walks through Central Park, I finally gave notice a couple of days ago. Before telling my CEO, I asked the Controller and CTO for their advice on how to give notice to him.  Our Controller has known about my decision to leave, since I tell him everything’s that’s going on in my life. The CTO’s response was great:

After your company was acquired, I was shocked you even stayed.  For me, every day you stayed was a bonus day for me.

reflection1Finally, I told my CEO that I was resigning.  He took off his glasses, and then wiped away one or two tears. He was surprised at the news,  because he thought I’d be there at least until the end of the year.

My little department is a well oiled machine, so I assured him that everything would be fine without me.

Food for Thought

I learned that there are times we must resign from your dream job. If you’re unable to perform your job to your own requirements, then you should exit.

I’ve also learned that telecommuting didn’t work in my case. In early stage companies, managers and leaders rely on impromptu meetings or quick talks in the hallway. Missing closed door talks, I no longer participated in critical conversations. These absences signaled to me that it was time to leave, despite how much I loved my work.


Unfortunately, things didn’t go well for my CEO and Executive team members. In May 2007, I received an email from one of my Marketing team members, asking me to be a reference because the company went out of business. I had to re-read the email several times just to make sure I read it correctly.

I called my former Product Marketing Manager to confirm the news, and then tried to call my other Executive team members. I finally got through to Controller, who told me of the operational issue that sunk the company. I left a message for my CEO, but knew he was too busy taking care of the crisis. All I kept thinking was how easy it is for a founder to lose all that they have worked for because of one act, by one employee.

Before the disaster hit, my CEO and Executive team were so close to being acquired. The exit strategy was nearly complete, and then the tragedy struck. I was heartbroken for my peers, but mostly for my CEO.

Post Mort-em

I’ll never experience another work environment like the one I had with my CEO’s company. I have nothing but fond memories of my peers and my Marketing team. I have no regrets, except I wish I could have been there during the crisis. But there is a reason for everything. Looking back, I wasn’t supposed to be there during that time.

I’ve checked in with former colleagues. They’ve mostly healed since May 2007. We all agree that the time we spent together was special and unique. From my perspective, it’s rare to find coworkers who as you bring out the best in you. If I work for another company, I hope to find a similar work culture, mimicking the one my CEO and our Executive team members created.

It’s not very often I have the privilege of working with such a noble man. I’ll always be grateful to my CEO for plucking me out of obscurity, having unshakable confidence in me, and allowing me express my management and leadership ideas. His company changed my life; it was the capstone on a career that I had worked on since 1997.

Like all of his other former employees say, “I would work for him again in a heartbeat.”

The Smart Lemming Diary is a series that chronicles a journey of laid-off worker, who becomes a Vice President of Sales Operations & Marketing for a small entrepreneurial healthcare technology company. For previous entries in this series, click here. For the first diary entry, click here. For the highlighted Smart Lemming Diary entries, click here.