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Why you should leave a startup

Why you should leave a startup

5 BASICS and 9 BOUNDED reasons to leave your current startup

Giammarco Pacifico & Federica Montrone
September 13, 2023

Joining a startup is great for many reasons.

Some of them have been explored in our newsletter series so far.

But there might come a time when this kind of opportunity does not suit you anymore.

The reasons why this happens vary a lot and understanding them deeply is fundamental to making the right choice.

As thoughts about leaving usually arise from a place of discomfort, acknowledging this feeling is the starting place to understand whether your only option is to leave your startup job or not.

Let’s start!

Reasons to leave fall into two broad categories: "BASICS" and "BOUNDED".

BASICS

BASICS reasons are not specifically related to the job you are doing or the company but to the nature of the startup world itself.

Startups are notoriously fast-changing environments, where people are asked to do more than what they’ve been strictly trained to do, and where structure might not be as clear as in big companies.

Well, not everybody can handle such an environment, which sometimes can rapidly become both exciting and tedious.

Some of the most pressing challenges might be the following:

Too much ambiguity
Clear instructions are hardly present. Ambiguity might be built into the problem to solve, or key pieces of information may never get to you. The only way to survive this is to never give up trying to get to the truth by making sense of the communication mess
Too hard to communicate
Healthy professional relationships rely on building effective communication. This is a general rule that applies to every kind of environment, but as a startup is made of few people, the interactions between a few colleagues are far more frequent and those need to be effective. The company's success and growth rely upon its talent but this harmony only builds up with being comfortable in handling hard conversations
Things change all the time
You need to always be prone to delays, unexpected results, and changing directions. All those changes are not for fainted hearts and it can be quite stressful to keep chasing new things every time rather than having them under control
Unstructured path
If you are looking for a clear ladder to climb, startups are not the right place. For all you know, your startup might be dead tomorrow and the only good reason to keep pushing is that you believe in the work you do together with your teammates. Gratifications like promotions and annual pay raises could follow but they are not a guarantee so be cautious about your expectations
Richness and social validation
Be wary of comparing yourself with your friend who works at a top consulting firm. They probably have different values which led them to a different choice. If you desire his life and perks, you better follow his path, rather than spend energy in a startup. Nobody assures you will become rich by working at a startup, nobody probably even knows the name of your company and the risk of failure is always around the corner. If you are optimizing for short-term income, reputation and job security, there are better choices than joining a startup.

Although an exaggeration of those features is never a good sign, these characteristics are typical of any startup environment and you better adapt to them or plan to move on.

You might be charmed by the mission of the company but be careful: your passion needs to be strong enough so that you can handle all of these things without stressing out.

Self-consciousness and clarity drive us to the best trade-off between what we want and what we can handle.

Because those are just BASIC reasons, if you are suffering from those, take some time to reflect on them and ask yourself: are you unhappy because you realised you’re not a startup person at all or it is just a turbulent moment that you need to figure out how to manage?

Leaving everything might not always be the right answer.

BOUNDED

However, there are other reasons that might make you jump to that conclusion instead.

We call these reasons BOUNDED because they are uniquely linked to the company management, culture, history and specific business opportunity.

These are more critical than the previous ones as they represent widespread company problems and should be taken into account much more seriously.

Some of these reason are:

Poor management
If you don't trust your management you should leave immediately. If you don't believe in your leaders who are making the most important decisions, you can try to speak up (although there is no guarantee they'd listen to you) but you better start looking for a better place
Slow at making decisions
Bureaucracy is cumbersome. Startups shouldn't be. If yours is, then it will probably not last very long and it will drawn in a sea of indecision and uncertainty. This is a huge red flag and you should leave a sinking ship ASAP (there is no pride in waiting for the unavoidable layoff when hard times come because it's only a matter of time before they will)
Teams are randomly built
Hiring is poor and only based on local resources. If you are building the next world-changing company, it is very unlikely that you will find all the talent in your local ecosystem. Hiring must be thoughtfully designed to attract diverse talents and make them excel together. If this is not happening the company is probably optimising for the cheapest (and easiest to get) talent, which is a major red flag
Poor communication
This does not mean that people don’t talk. They rather don’t exchange meaningful information. In a place where life or death depends on effective communication rather than on standard procedures, this is a recipe for disaster
Competitors are following totally different paths
Competition is there for the company to raise the bar and define the rules of the game. Unless your company is in a blue ocean, going in a totally different direction than competitors for its own sake is not wise (unless there is a secret sauce that justifies a contrarian view)
Current investors are not leading the next rounds
The company might be already a walking dead (aka waiting for the capital to finish before winding down) and investors are waiting for its day to come. Of course, current investors might simply not have the follow-on capital to invest but in that case, they’d have no problem finding other investors, if they still believe the company represents a unique investment opportunity
No stock option plan
This alone is usually not enough to leave a startup but no option pool for employees means that the company does not value attracting the best talent and does not care about incentivizing them to go above and beyond.
Why would that do that? Because of greed (saving 5-10% of the company for themselves) or arrogance (no need for ambitious go-getters and preference for pawns that execute orders)
Poor work culture
This is obviously never a good sign. But how to spot one? Look for these cues: management finds it hard to delegate, you always need to ask for permission to do everything, and the company doesn’t easily promote people, nor does it fire anyone
You can't find a professional mentor around you
Structured mentorship is usually absent in every startup as your manager is probably juggling a thousand things.
However, if you are a young professional and do not admire anyone in your company, you should look for a place where you want to become like the people above you. Mentorship happens in many ways and following the lead of someone you truly admire is the easiest path to build a great career for yourself.

Of course, there are many more reasons, some might be linked to personal or family situations, others to relocation needs that are beyond our control.

In other instances, the company vision simply doesn't align with your ambition anymore and that’s usually a good reason to leave.

It is however important to start with the basics and then understand whether it is time to untie the bounds.

Until next time,
Federica

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