Can I Go Back to Having a Boss?

For many of us, the thought of becoming the employee once again may feel like a monumental step backward.

We worked so hard to be in a position to forge our own path that reversing course feels like total failure.

But the reality is being an employee again does have its advantages. Even if we decide to go back to being a Founder afterward.

I'm a Founder — how could I be an employee again?

It may be a terrible outcome.

The very nature of most Founders is that we generally don't like being told what to do. It's kind of our thing. It doesn't mean we're horrible people (right?), it just means we're naturally comfortable in leadership roles.

That's why most leaders are leaders.

It's not a subtle change. Once we've had total autonomy it's kind of hard to go back to a subordinate role. It's like moving back in with our parents. It may be "safer" for a minute, but there's a reason we moved out to begin with!

Are there any upsides to being an employee again?

Actually yes.

For starters, it may feel like a bit of a "breather" from having the weight of the entire company on our shoulders all of the time. It'll also be nice for the major problems to be someone else's problem for a change.

It also gives us an opportunity to learn again. We can start to pick up skills from our new managers that we may have been lacking in our last role, such as organizational development or specific skills we were lacking in our last go around.

A good way to think about our time as an employee is a training ground before we take our next leap.

What if I never go back to being a Founder?

That happens a lot actually.

One of the things that we don't talk about much is that while being a Founder feels noble and liberating, it's also a really stressful path that becomes far less compatible with different stages of life, from having a family to recovering from debt.

What's nice is that we've seen what the other side looks like, so we can make a strong decision either way. In this case, the optionality is a big win.

In Case You Missed It

Am I a Fraud? (podcast). As a Founder, when was the last time you felt like you had no idea what you were doing? Join Wil and Ryan as they discuss why feeling like a fraud is actually a very normal part of Founder life.

The Myth of Job Security. If a job can be lost at any time because of external factors, why not work instead on something you actually care about?

Why Good Employees Leave High Paying Jobs. If companies want to attract and retain the best talent, they have to start moving toward a “culture of feedback” that ultimately just means the ability to have honest conversations.