How I almost quit because of $75

Lessons learned from considering quitting 3 times

Working in tech has a lot of highs and lows. During the lows, the thought of switching companies always comes to our mind.

People rarely talk about the ‘almost’s. The instances when you almost quit, but decided to stay. Today, I decided to share my experiences.

3 times I was close to quitting (once a year 😅) and each one of them taught me some useful lessons.

❌ First time - $75 and righteous anger

It happened right after I was promoted to a team leader role, ~14 months after I started working for the company. It was in December, near the end of the year.

After the transition was finalized, I wanted us to have some fun together as a team. I found a nearby escape room and booked it for all of us for $175, assuming reimbursement would be easy to get.

When I asked for it, I was told that the team already finished the budget for the year, and the maximum I can have is $20 per person ($100 total).

That made me really angry. I mean - come on. Who cares about yearly budgets, it’s just $175. I’m a newly appointed team leader, and I want to do some bonding with my team - why can’t we have some fun?

I decided I would cover the difference, and that afterward my righteous anger would get the expense approved. No such luck.

Infuriating, right? A company that raised $100M in VC money can’t spare $175 for people to have fun? Isn’t the morale of the people a top priority for them? I was thinking that I don’t want to be a team leader in such a company, with a perverse set of priorities.

… And that’s one side of the story.

But what if I told it a bit differently:

• There is a yearly budget for each team. It’s not big, but it covers multiple team events a year.

• The company is frugal, as we are in a tough industry (AgTech). Money is spent where it’s most needed - on salaries and the business.

• Team ‘X’ finished their yearly budget.

• Then comes this newly promoted guy, who insists on doing another team activity right now. Even though it was outside of budget, we were able to come up with something for them.

• The new TL insists on going to an escape room (and not bowling or a team lunch, which are cheaper) for some reason, and cannot wait for 2 months for the next budget.

• He insists that he will not allow his team members to pay $15 and that he will have to pay it himself if we don’t approve.

• Fuck that guy 🖕 (I wasn’t told that, but in hindsight, I would have said it to myself).

Do I still think I should have gotten the budget? Yes.

Was I a spoiled brat who focused on the completely wrong things? Yes.

Why did I decide to stay

Honestly, I was not THAT close to quitting. I considered it, but I loved the people, the tech challenges were interesting, and I was just promoted. So once I cooled down, it was an easy choice.

What I learned

Being angry and righteous is a waste of time and energy

I should have focused on what I wanted to achieve. Budget exists for a reason. I appreciate the frugality of my company - this is how we are still in business in 2024, in a very tough market. And who cares about the type of the team activity?

My head was responsible for 95% of the conflict.

❌ Second time - getting bored

Performance review time arrived. Mine was pretty good overall, but there were some key areas to improve - reducing the dependency on myself (a challenge for anyone who was promoted to manage their previous team), hiring additional developers, and taking more responsibilities as a team.

Fast forward a year, and I ticked all the boxes. I’ve hired 3 developers, the team was performing well, and I got an excellent review.

I was bored. After 2.5 years in the same team, there were not many new challenges. It was the beginning of 2023, and we knew the layoffs wave wouldn’t skip us, and there was no plan for growth in the near future.

I started to look for new challenges. I considered different paths - starting something of my own, going to work for a VC, or joining a very early startup as a VP R&D (surprisingly, I got 2 such offers).

Why did I decide to stay

I didn’t really want to leave the team I’ve built. We had a good thing going on, and I enjoyed coming to work. In addition, my wife was pregnant, and I thought that a better time for a change would be after the paternity leave.

I decided to give it a few more months, and I made sure my manager knew that I wanted to do something different once I returned.

In parallel, I started to challenge myself in other areas - that’s when I started posting on LinkedIn.

What I learned

You can find your challenges outside work!

If you enjoy your day-to-day, and like the people you work with - don’t be hasty to look for bigger challenges. That year of writing on LinkedIn (and later on, this newsletter) provided me with TONS of challenges, experiences, and valuable lessons. If I had switched jobs, I would have never had the mental capacity for it.

❌ Third time - feeling exhausted

So I returned from paternity leave 3 months ago, back to the same role. Our sales didn’t go too well, and together with my manager, we decided to postpone any changes.

Then 2024 arrived. I suspected layoffs may be planned, and I was very tempted to ask to be part of it.

My wife had a tough time with our baby, and I wanted to join her for a few months. In addition, as I was already on the fence anyway, I could save someone else from being fired.

And finally - after 3.5 years, I wanted some new challenges.

Why did I decide to stay

1. The one thing that hasn’t changed from day one - I still love the people I worked with. I have a strong team, and my peers were all awesome.

2. I believe in the new direction of the company. Our CEO has made some tough decisions and decided to focus on 2 areas that I felt are the right choice.

3. But mainly - because of my manager. After 2.5 years of managing me, he knows me well, and we have a great relationship. He offered me more responsibilities in areas I enjoyed working on, and I decided to trust his judgment.

What I learned

During our long discussions about the future, my manager told me something I’ll remember: “The longer you stay in one place, the more influence you have. The truly great things I did, were always after a few years in one place”.

Final words

The are many advantages to switching companies, such as:

• A higher salary

• Getting to know more people

• Learning a new technology and industry

There is no right approach - everyone makes their own career choices. So far, for me, the decision to overcome the urge to quit and stay - was always a good one.

What I enjoyed reading this week:

1. A sneak peek into the future of the usage of LLMs in software development in

   Engineer’s Codex
   - saving time for developers, without creating tons of bugs.

2. 5 mistakes that make your documents terrible in

   Techlead Mentor
   - great tips for writing good technical documents.

3. Behind the scenes of your performance review in

   The Curious Soul's Corner
   - a staff engineer’s take on performance reviews.