I made a lot of mistakes at my first software job. We all do, mistakes are a natural part of growing. However where I particularly screwed up was how long I persisted and stayed at my organization. I stayed for 5 years - that’s a long time for your first job! During those 5 years the company went through a lot: an acquisition, two rounds of layoffs, talented senior engineers fleeing the company, the organization being switched into ‘harvest mode’, our CEO and GM being charged and fined by the SEC for fraud, a failed AWS migration, and another change of leadership.

Throughout all of this, I stayed. I commiserated with coworkers, and listened when they tried to convince me to leave. I even took a few calls here and there for other roles. But no matter what, I stayed.

It wasn’t compensation keeping me - unfortunately compensation increases in our industry tends to come from job hopping, not staying in one place. It was doubt. Every time I thought about leaving, I was plagued with it. Was it the right decision? Was I missing out by leaving?

Here are some of the doubts I’ve had over the years, and why they’re unfounded. Deciding to leave a job is hard. Hopefully one of these will help you better approach your situation.

I can’t leave now - the company is improving!

If you’ve stayed at a company during its downward spiral, you know that it’s hard to give up. You’ve spent so much time at the organization, you feel invested in its success. It’s natural to get FOMO. “What if I leave and the company begins to turnaround?”

I’ve listened to this fear and persisted through the whole process, from the downward trajectory all the way to the business turnaround. It’s not worth it. It’s a long process that takes years. To be a part of it isn’t a grand adventure - it’s a hard slog.

In my experience the turnaround takes place by leaning on engineers to push out more features. All the technical and infrastructure debt that’s holding your organization back? Even after the turnaround you likely won’t be able to tackle the majority of it. It’ll still be there.

To top it off - during the turnaround, you won’t be compensated well. If you’re unhappy with your compensation now, just wait until three years later. Your peers at other companies will be earning tens of thousands of dollars more than you, just because you made the decision to stay and they didn’t.

There’s no sunshine at the end of the rainbow here. The process of turning a company around is a brutal one. Don’t commit yourself to it lightly.

The acquisition won’t be that bad! Leadership is telling us it’s fine

I’m sure they are. Being acquired is usually terrible. There can be good acquisitions, however my opinion is that they are few and far between.

Regardless of it’s outcome, every acquisition is acompanied by the senior leadership team telling everyone that everything will be fine. They’ll do it across every communication channel possible, in person 1x1s, all hands meetings, emails. Common refrains include:

  • “The acquisition makes us stronger than before!”
  • “For the vast majority of you, nothing will change”
  • “They’ll only be a slight consolidation of similar roles”

These are mostly lies. Usually the senior leadership team of the company getting acquired are being paid a lot to reassure people. Most leaders will be compelled to stay by ‘golden handcuffs’, an equity grant that keeps them at their role for a year to provide stability during the transition. Afterwards they’ll likely quickly leave, bringing their favorite talent along with them. Watch what they do, not what they say.

Take an acquisition for the sign that it is, that the combined company is likely not going to be a place you want to work at. Don’t make my mistake - leave.

Everyone else is leaving, I have a responsibility to stay and fix things

No, you don’t. Unless your organization is actively saving lives, or you own it, you have to keep in mind: your number one responsibility is yourself. You likely have a partner, family or community you need to provide for. To do that well, you need to focus on making sure you:

  1. Enjoy your work
  2. Are compensated well
  3. Work reasonable hours

Your entire organization is not your responsibility. Have the courage to change the things you can, but accept the things that you can’t change.1

You’re going to have a long, tiring career ahead of you if you spend it trying to fix broken organizations. Wouldn’t you rather leave and work to build something great instead?

But the tech bubble is going to crash any moment now - what if I get laid off and can’t find a job?

This plagued me during every job search - “But what if the economy crashes and I get laid off from my new role?”

This actually happened to a friend of mine - they left our company for a new job. Within a few months of joining the new company Covid-19 hit, and they were laid off. However they talked to friends at our company and got hired right back on a new team. Most likely with a compensation increase! It’s so common we have a term for it, a boomerang hire.

As for me, I started my job search during the full brunt of Covid-19 in Spring 2020. I had more recruiter calls, job leads, and opportunities than I could keep track of.

There’s always a market for good talent. If you know that you are good at what you do, even during a downturn there will be people who desperately want to hire you. Don’t let the fear of disaster keep you from reaching out for something more.

But the people I work with are amazing!

I’m sure they are. There’s also amazing people at other companies. Would you accept a job at a company where you didn’t like your interviewers? Doubtful. Trust that you’ll steer yourself towards another place with wonderful people.

I’ve built so many relationships that help me get my job done. Am I really going to throw those all away?

Yes, you will. You’ve built these relationships before, and you’ll build them again at a new role.

Also, you are not throwing them away! Those relationships will last a lifetime and will be an invaluable source of future job opportunities as well as referall hires for you. Keeping in touch is easy nowadays.

My team won’t be able to survive without out me!

Ego, ego, ego. Teams are incredibly resilient things. While a key member leaving will often throw things out of balance, with time teams will hire and heal themselves. Often a senior person leaving gives a more junior engineer an opportunity to step up that they wouldn’t otherwise have.

Make the choice

There are benefits to staying during a tough period for a company. However, the opportunity costs (the loss of potential gains from alternatives) are likely far higher. Trust your gut if it’s telling you to leave, and find the role that’s right for you. Our lives are finite, spend it doing something you love.