Quitting my job without a plan

(If you haven’t read Part 1 – The Build-Up, click here.)

So I had made the decision to leave. There was a gap between the time that I made the decision and the time that I actually quit for a couple of reasons. I’d be lying if I said it wasn’t a little harder to stay motivated during that time, but my “why” hadn’t changed. I’d stayed as long as I did because of the people. I cared deeply for many of my coworkers and mentors, and I absolutely loved the people that had worked for me. Plus if you’re going to spend time on something, anything, might as well take it as far as you can.

There were a couple of things that made it harder to leave. There were a couple that made it easier. But honestly, it was pretty uneventful. Aside from the “where we going?” message I got from someone when they heard I had given my notice.

So for this part of the story, I want to focus on the biggest lessons I learned while I was there.

Lesson 1: Aim to make yourself replaceable.

From early on in my career, I told myself that I would never be the type of person that tries to hang on to my position, to consolidate power, to prioritize self-preservation over what’s best for the business.

This served me well.

Since a year after I became a manager, I was constantly trying to develop someone to replace me. Maybe it was in one of the books I read early on, but it just made sense to me.

When you focus on making yourself replaceable:

• you accomplish more because you empower instead of delegate
• the people the work for you go further, faster
• you stop associating your self-worth with your position
• you set your sights higher, on what you need to learn for the next role.

I’ll give this approach a lot of credit for the following.

This image represents the people that worked for me. Of about 40 employees over this time:

• 5 have started or are starting their own companies
• 10 are now in management
• 2 quit, and it was the right move for both of them
• I’m still in contact with most of them.

Obviously I’m not taking credit for what these people are doing. But they say you should judge a leader by the accomplishments of their people. However I’m judged, I’m damn proud of this.

Lesson 2: Don’t worry about getting fired.

Obviously, this is not an endorsement to be a ***k. Some people go way too far. But much more common, we overestimate the risk of speaking up. Being bold. Asking for what you want. Bringing up problems, especially if it’s something your boss is doing.

Overall, this is about prioritizing what you think is right over self-preservation. This is about prioritizing truth over loyalty.

Pick the organizational disaster of your choice. From Enron to the Houston Astros to the Minnesota Police Department. Somewhere along the way, many times along the way, people made the decision to be loyal to bosses, colleagues, peers instead of telling the truth. It doesn’t end well.

This is about being able to live with yourself. Not having regrets. Knowing that you did what you knew in your heart was right.

When you do this:

• you focus on what’s important because you prioritize impact over perception
• you build better relationships with peers because you prioritize accomplishment over competition
• you stop bad things from happening.

If it wasn’t for this, I probably wouldn’t have gotten that first management position.

Lesson 3: Say yes to fun work.

When faced with the decision whether to do something, fun should override most other factors. Especially at work. Taking on the job of running Latin America was so much fun. That crazy night celebrating some futbol match (that apparently mattered a lot) with the locals at the Obelisco in Buenos Aires.

Not sure if that was rain or beer on us…probably both.

Spending (not enough) time in Bogota working with and building the team there was amazing. They’ll always feel like family to me.

After I became a manager, when the chance came up I would take on a consulting project. Partially to keep my technical skills from slipping too far, but honestly I just love consulting. Working with people to help them solve problems. There was one project that probably should’ve taken two months, but for lots of reasons, the client wanted it done in one week. So I took that one on. One full week locked in a conference room with a rotating group of six people client-side, to complete a project, end-to-end, that should’ve been two months. And they made it very clear they weren’t going to pay a penny more than 40 hours worth.

There was some problem that I was trying to figure out. Some formula or something. So I sat back in my chair for a second, searching my brain and the room for the answer. No sooner than my first blink “are you waiting on something from us? do you need something? what can I do?” Yadda yadda, we pulled it off. That was 5 years ago. We haven’t really kept in touch. But just last week a friend was talking to that same client and they brought up my name, that project.

When I quit, I gave about a month’s notice. Aside from documenting the projects I had in flight, it didn’t make a ton of sense for me to keep pushing on other work if I wasn’t going to continue it. So I had some spare time and I asked if there were any interesting consulting projects that I could help with. There was. It was a discovery, my favorite. There’s just something about digging into a problem to uncover the root of it that I love. Especially complex problems that, on the surface, look simple. But almost always the root cause lies within the people and the culture. Figuring that out and solving it is just so damn fun.

We’ll talk a little more about that project through the series because it didn’t wrap up before I left the company. Plus it had a lot to do with where I am now…

But anytime I had a decision about what to do, and went with the most fun option. I never regretted it.

Lesson 4: Everything is temporary.

In 6 years at one company, I had 6 different jobs. Several of them overlapping. At one point, I had 3 at the same time. Don’t do that…

A good friend asked me which was my favorite and I honestly couldn’t answer. I learned so much at every step and miss something about every position. There’s also things that I hated about every position. No matter the job, some part of it kinda sucks. Just can’t let that ratio go too far the wrong way.

Looking back, I certainly stressed and worried much more than I needed to. It came from a desire to do a great job, but until recently, I didn’t have the ability to be at peace with the gap between how things were and how I want them to be.

This is all about acceptance, clarity, and awareness.
Acceptance of how the current situation is.
Clarity into how you want it to be different.
Awareness that every current situation is just that, current. It will change.

With this, we can get a little more comfortable with that gap.

Acceptance was the part that I lacked. I was pissed off at the difference between how things were and how I thought they should be. That caused both good and bad things. That helped me work really hard to make them better. But it also kept me from appreciating the good things along the way.

I was too focused on closing that gap. With a little more acceptance, I would have been happier and probably accomplished just as much if not more. I would’ve recognized that everything is constantly changing and won’t last. When we do that, we persist through the bad a little easier and appreciate the good even more.

It’s hard to put a value on an increase in overall happiness level for 6 years, but it’s high. And recognizing the impermanence of every situation would’ve made that difference.

Now what?

Boiling down my time there to 4 lessons doesn’t do it justice. I’m a completely different person than when I started, certainly for the better. I’m infinitely grateful for the people I got to work with, many of which are my best friends now.

My time there had come to a close and I had no idea what I was going to do next. But I knew one thing. I was going to take a damn break.

Next up in the series, The Summer of Matt.