Making the decision to leave

Reasons I've left my previous roles

I’ve been in job search mode for the past couple of months, which has shown in recent topics how I look for a new job and what to ask your interviewers. My search concluded recently when I began my new role as a Staff Software Engineer at Memora Health. Even so, I’m still reflecting on the transition.

If you are in your first or second FTE (full-time employee) role, deciding when to leave can be challenging. If you were previously in academic or contract environments, you had an end date more or less set for you. As an FTE, you make the decision to leave on your own.

This can be a difficult and emotional experience! You might feel a sense of loyalty to the company or your manager for taking a chance on you. You might feel like you would leave your teammates short-staffed. You might be worried about the unknown. It can lead to a maelstrom of conflicting feelings around what is undeniably a big career and life decision.

It’s also important to acknowledge that not everyone gets to make the choice for themselves. Many leave their jobs due to external factors. Layoffs are top of mind in the tech industry right now, but other external reasons include health issues, family commitments, return-to-office policies, or any number of other situations you have no control over.

For those who are in the position to make their own decision, every situation is unique and it is difficult to give blanket advice. Sometimes leaving is obviously the right thing to do (toxic work environment, you find out you are very underpaid, etc). Sometimes leaving is obviously the wrong thing to do (as an overreaction to constructive feedback, the company stopped stocking your favorite snack in the kitchen, etc). There is a lot of grey area between the two extremes.

But perhaps some examples can help you think through it. In this post, I’ll walk through why I decided to leave each of my previous roles. There’s often more than one reason, so I’ll focus on the primary driving force rather than the specific last straw.

Boredom

Microsoft, three years in.

After three years on the same team, performing the same tasks, I became bored. This was my first FTE role and I didn’t recognize the signs of my gradually increasing boredom. I’d never worked on anything for three whole years before! As my ennui increased, I reluctantly dragged myself to work until one day a switch flipped in my head. I realized that I needed to leave. I couldn’t bear continuing to do the same things over and over.

What I learned from this experience was how important it is to recognize the early signs of boredom and burnout. I’ve gotten much better at catching those early and working with my manager to shift my project, team, role, or whatever is necessary to keep things fresh and interesting.

Now that I am much further along in my career, I’ve come to the conclusion that everyone has a certain time span they can focus on a project before they become disinterested. This time span varies greatly from person to person. For me, it’s around 18 months. This doesn’t mean I have to switch companies every year and a half, but I do need a major change.

Detachment

Caradigm, six months in.

I went to work each day completely detached. I wasn’t invested in the company’s mission, the products didn’t interest me, the tech stack was unappealing, and the team lacked any sense of camaraderie. There was simply no reason for me to be there.

I ended up staying for an additional three months to finish a major release out of respect for the Product Manager. That PM was a ray of light in a dismal place and to this day is still my favorite PM I’ve ever worked with.

What I learned from this experience was that in trying to get away from the boredom of my previous role, I’d jumped too quickly at the first offer to come my way. I hadn’t sufficiently considered what I wanted. Since then I’ve been much more deliberate when choosing a new role, to the point where I usually take significant time off between roles to make sure I’m making decisions with a clear head.

Project Cancelled

DocuSign, two years in.

I’ll mention this one even though I ended up staying in the end.

This experience was quite the opposite of the previous one. I was deeply invested in a project I had been building for two years, only for it to be abruptly canceled. I understood the company’s reasons for the cancellation, but at the time it felt very personal. I had poured a lot of time, effort, and myself into this project. It was my baby.

I was strongly considering leaving when another manager offered me the opportunity to join their team and work on a project of my choosing. It wasn’t quite a diving save, but it sure felt like it.

And I’ll never forget it.

Outside Interests

DocuSign, six years in.

The previous instances were all the result of something happening with my work. This transition was the first time that I was lured out rather than repelled from within. Through six years at DocuSign, I successfully navigated various teams and roles, warding off boredom and burnout by making timely changes. The people were excellent and the company treated me well. It was truly a solid place to work.

While I was there I helped build up the engineering intern program and over the years I became increasingly interested in the recruitment space. Specifically the problem of how companies and candidates discover and evaluate each other. I eventually decided to leave to immerse myself in that problem space.

What I learned from this experience was that sometimes it is just time to move on. There doesn’t have to be anything wrong with your current role.

Levelling Dispute

SeekOut, 18 months in.

When I started, the company had a very broad, lightly-defined, Senior level that I was placed in. Later on, the company decided to establish a more formal engineering career ladder. Engineering leadership invested significant time in determining and documenting the expectations for each level. As part of this, they decided to split the Senior band into Senior 1 and Senior 2, which I’m going to call Senior and Staff here because it’s less confusing.

Having read through the documentation, I was confident that I was operating at the high end of Staff. So I was surprised to learn that management had placed me at the high end of Senior. As we discussed, it became clear that my manager felt I was performing at the Staff level, but I was held back on (what seemed to me) a technicality. The rule was that you couldn’t be Staff unless you checked every box for Senior and there was a box that I couldn’t check because of the structure of my team (that was outside my control).

I wasn’t willing to be considered by the company to be a full level below my actual contributions and responsibilities. We tried to work it out but weren’t able to come to agreement, so I left.

What I learned from this experience is that sometimes you need to think about your long-term career. Even if you have a great team and project, if staying will negatively impact your career 5 years out, it might be time to leave. This is, to date, the only time I’ve had to leave for career advancement reasons.

Project Takeover

AudioEye, 5 months in.

The main driver for my departure was a truly bizarre takeover of my project. During my week off, it was announced that the CTO had become the Chief Strategy Officer (CSO), relinquishing control of the Product and Engineering organizations to become a C-level independent contributor. As part of this transition, the CSO took control of my project and team, directing the team to essentially discard our existing work to pursue entirely different objectives.

I found both the change and the way it was carried out profoundly disrespectful, and I immediately started looking for new opportunities.

To be as fair as possible, I did hear the CSO’s version of the story a few weeks later. It was a starkly different narrative that positioned the CSO as the hero. In fact, they appeared somewhat surprised that I didn’t appreciate their efforts. For the record, I remain convinced that my interpretations were more accurate.

But the experience offers several important lessons:

1. Give advance notice. When major changes are pending, inform in advance those who will be most impacted. Time and again, I’ve seen how a simple heads-up and actually listening to people’s concerns can clear up half the angst and distress you would otherwise get.

2. Tell a story. In the absence of a story, people will create their own, making assumptions to fill the gaps in their limited information. If you are responsible for a change, it is essential to provide a clear explanation rather than leaving it to every individual to devise their own conflicting narratives.

3. Sometimes you are the villain. The villains in your stories rarely see themselves as such. In the same way, you will inevitably be the villain in someone else’s story. And that’s okay! When that happens to you, explain your version of the story as best you can and then move on. Make decisions you believe are right.

I’ll leave it at that

Well that was quite the trip down memory lane. I hope my examples have given you some food for thought or, at the very least, some entertainment.

Do you have a fun story about leaving a job that you’d like to share? Leave a comment or send it to virtualmentor@substack.com