It was 2005, but I remember it clearly. I was working for a company that was quickly making its way up the Fortune 500, and its desire to extend the business internationally was causing us to stretch in new, uncomfortable ways. A large consulting company that had “done this kind of thing before” was now running the show, and our CIO was leaving in the midst of lots of rumor and turmoil. On his last day, the CIO, who had capably led us through many other challenges in his eight years with the company, stood before us with tears in his eyes. We were a Technology team of 1000 people.

“I’ve failed you,” he said, “and now I’m leaving.”

The consultants had convinced my company that outsourcing its Technology department would both improve performance and save money. Our CIO had fought the decision with all he had, but in the end, it wasn’t enough. As we watched him leave, the reality of the situation sunk in: the rest of us weren’t going anywhere, at least for the time being. Was our CIO leaving because he was outvoted on the outsourcing decision? Was he leaving because his ego couldn’t take the hit?

Had our captain abandoned our ship, jumping into a small lifeboat and leaving us to drown?

The writing on the wall

Last December, after more than five years at my previous company, I left to join SportsEngine as VP of Product and User Experience. Leaving my job was one of the hardest decisions of my career – in partnership with some of my favorite co-workers ever, I’d built an amazing team from the ground up. If you’ve read any of my previous posts, you know the team I was leaving was forward-thinking and creative, that we were lean and Agile, and that we were high performing.

When I started exploring other options, I knew that the reasons to stay were significant and plentiful: my co-workers were great, I was respected, and I had the opportunity to make a meaningful impact. For months before I left I would meet up with friends and float the idea of finding a new gig. They looked at me like I had two heads. “How could you leave?,” they asked, “it sounds perfect.” From the outside looking in, I was in an ideal spot. Each time I met with a friend I returned to my office determined to make it work. What was I thinking?

But the writing was on the wall. The company was struggling, and I was struggling to grow there. I had all sorts of ideas about how to make things better – org changes, new hires, process changes, new focus areas, and more – but my suggestions went nowhere. I’ve written in the past about people who have the wrong attitude and how toxic that can be, and I did my best to address those situations when they arose in myself and in others. I looked for new angles, different ways to approach our problems, short- and long-term solutions. Over the course of almost a year, I exhausted every path I could identify. My frustration grew. I didn’t – and I don’t – blame my boss or the company for failing to see how “brilliant” my suggestions were. My knowledge was limited in some ways, and my ideas were rooted in my own biases. It’s very possible that some of my ideas were uninformed, impossible, or just plain bad.

Through it all, my team continued to perform terrifically. At our annual offsite, the CEO told the group we were among the company’s highest performers, and the team grew as other areas in the business were consolidated and moved. Our team was highly motivated, delivering great work and usually feeling both valuable and valued. But if I couldn’t extend my influence beyond my team, I knew the honeymoon wouldn’t last. And I knew I wouldn’t last either.

Who’s the captain?

All of which brings us back to the CIO at the start of this post – the man who left his large team at sea. Did he do the right thing?

Of all the reasons to stay at my company, the biggest was guilt. As I mentioned above, I’d built my team from scratch, and I’d played a role in the hiring of nearly everyone on it. My closest coworkers were also close friends. How could I abandon them? To make matters worse, the company wasn’t doing well. As a leader, wasn’t my job to rally the troops? If the ship was sinking, shouldn’t I be sinking with it?

I questioned my own motives for wanting to leave. For the most part, I felt listened to and valued, even as my best ideas languished on the sidelines. My relationships were strong, and I was assured that my future at the company was bright. I was frustrated, but not angry. Was my ego getting in the way of my desire to stand by my team? After some reflection, I decided it wasn’t. I was just getting my head around something I’d realized before but hadn’t really accepted: I might have been the captain of my team, but I was clearly not the captain of the company.

Months ago, in a blog post about getting fired, I wrote:

After we’ve said our piece, when the dust has settled and we didn’t get our way, our choices are clear: we can change our attitude, or we can change our scenery.

It was time.

Leaving can create opportunity 

There were lots of good reasons for me to leave my company, including career growth, opportunity, interesting new challenges, general well-being, and more. Several people on my team saw that it was also an opportunity for them. If I felt like I was stagnating in my role, looking for ways to extend my influence, there were others who felt that way too. The last thing I wanted to do was hold good people back.

When I eventually left the company, several people had the opportunity to grow in their roles, to lead bigger teams and to drive bigger decisions. The team I’d helped create continued to evolve, and was, in lots of ways, self-sustaining. It was ready for new leadership and ideas. Despite my best efforts, I had to acknowledge that my own ideas and approach weren’t working.

The CIO at the start of this post knew the same thing about his Technology team. He knew we had to become what the company needed now, rather than the thing he’d built. His leaving was an acknowledgment that the company was changing, that he was not the captain, and that he understood his own limits. He was stepping aside – at least partly – so that new leaders could emerge, and so the group could evolve and grow without being constrained by the “old guard.” I like to think that I was doing that too.

Fortune favors the bold

Maybe I’m rationalizing in order to make myself feel better. I’ve spent some time with my previous team members these past few weeks and things have been hard. The company’s going through lots of change, and the new leaders who are learning to step up are doing it in extraordinary circumstances. For some, it’s the opportunity of a lifetime, a crash course in business and leadership. It’s not easy, but that’s okay.

The decision to leave a job is a very personal one, with lots of professional, practical, and emotional considerations. The idea of a captain (or worse, rats!) abandoning a sinking ship has been so ingrained in our culture that it can be impossible to see beyond. But this is an unfair over-simplification. There’s a difference between abandoning ship and knowing when moving on is the right call for yourself and your team.

A company will do what it needs to in order to survive and thrive, and that’s a good thing; that’s what it’s supposed to do. Still, despite certain Supreme Court decisions, companies are not people, and they don’t have feelings. We need to be able to understand this, and to make decisions about our careers accordingly. Too many of us are afraid to be perceived as captains abandoning ship when we should be embracing a more relevant, empowering truth: fortune favors the bold.