Should I Stay, or Should I Go?

Out of all the topics I hear the most questions about is the decision to stay or leave at an early-stage startup.

I get it. I’ve been there myself several times.

What’s unique about the decision to go when you’ve been an early employee is how enmeshed you might feel about the company and role. These feelings can be attributed to the environment. To be hired as an early team member, you have likely been a foundational part of building the company and feel very invested emotionally and, likely, financially. 

In this post, I’ll share the advice I typically give someone when they ask, “I don’t know if I should leave.” 

Don’t hang on the side of the boat

It’s pretty common for folks who are wavering with the decision of leaving to “hang on the side of the boat.” By that, I mean they aren’t fully committed (on the boat) and, therefore, put themself in an agonizing limbo stage similar to hanging off the side of a speedboat.

It’s choppy, it’s unpleasant, and frankly, it’s stressful.

Meanwhile, their work output is typically degrading, and their attitude/engagement is also noticeably suffering, pushing them further down a path of unhappiness.

Occasionally, this can lead to the decision to leave to not be on their terms. 

A straightforward hack: pick a date to decide by and stick to it. 

Having a date to decide by can relieve a lot of the stress of feeling like we need to make a decision TODAY and let us take some time to consider the right choice rather than being rash or making an emotional choice. 

The timeline should give you enough time to get the answers you need. Perhaps that’s after your following performance review, the end of a quarter or year, after a big project or feature you’re working on has shipped. 

Deciding on a date will likely empower you to feel more in control and make the best choice. 

Identify Your Pain Point(s) 

For many, they may start to feel it may be time to go, or they may have a laundry list of things contributing to looking elsewhere. Gathering your thoughts and identifying what is leading to these feelings can help the decision-making process. 

A common pain point I hear from folks deciding if they should leave is not getting promoted after a few years in a role.

My response— have you talked to your manager about what is needed to get promoted? Do you know if the company needs someone more senior in this role?

Having candid conversations around the feasibility and business case for a promotion can give you more context on whether this pain point can be addressed or will continue. 

If your pain points are related to not having context or understanding, the best way to get clarity is to ask. While leadership can read your Slacks, they can’t read your mind. 

Stack Rank Your Life

One time, while hanging on the side of a boat, I met with a mentor who had me do an exercise. Looking at my life, I was to stack rank the top three most important things from a list of about a hundred criteria. The list included money, time with friends, being creative, physical fitness, getting promoted, being an active parent, etc. Once I honed in on my top three, I looked at how my current situation was tracking to the list. It was beneficial to look at the job and how the rest of my life was contributing (or not) to the big three.    

General Signs It’s Time to Go

While some may seem obvious, many folks still waver when faced with these signs. Here is my list of general signs it is time to move on from an early company. 

• You no longer believe in the mission or direction of the business. 

• You do not believe in the leadership team. 

• You’re beyond burned out.

• You’re reporting to someone who doesn’t advocate for you.

• You’re on a PIP.

• You’re more negative than positive. Prolonged feelings of pessimism. 

• The company isn’t doing well, and you have another offer.

• Your values do not align with the company, and it really bothers you.

Leave on Good Terms

Once you’ve decided to leave, the most challenging part might be one that is overlooked— leaving on good terms. I can’t count the number of times I’ve seen an early-stage employee crash land on their way out the door and ruin years of building respect and positive connections with their coworkers, manager, and leadership team. While you may be on the way out, distracting the existing team with your personal business or stoking internal fear is a surefire way to look bad. 

Leaving with grace, gratitude, and respect will not only leave you with fewer regrets in hindsight but can boost an already stellar reputation.

And maybe help you land a future role!