Being part of a startup can be both challenging and fun. Whether you are the founder or an early-stage employee. Working at a startup takes a special personality when you comparing the way startups do things to established companies. Even as an employee of a startup you are being entrepreneurial And entrepreneurship is not right for everyone. My most recent book, “The Ladder or The Grind”, talks about how to make the career choice between employee and entrepreneur. Today, I want to help you answer the question (Should I work at a startup?) by walking you through some of the reasons you should and shouldn’t consider working at a startup.

Reasons you shouldn’t work at a startup

Most of the professionals I meet fit into this category. They might think that it sounds exciting to work at an early-stage startup. But that isn’t always the case. Actually, working at a startup can be just as frustrating as working at a large corporation. It all depends on what you are looking for in a career.

Here a few reasons that you shouldn’t work at a startup.

You need consistent income

Working at a startup is a lot like being part of a research firm that funds itself through one grant after another. Many startups having to raise multiple rounds of funding. Which means if for some reason the startup you are working for runs into trouble raising additional funding then you could be out of a job. Now, you might be saying to yourself that established companies lay people off all the time. That’s true. Especially with the challenging economic times that the U.S. is experiencing right now. However, statistically, the highest rate of layoffs in an industry is around 3%. The failure rate of startups is dramatically higher than that.

You need structure

If you are the type of professional that needs a lot of structure to your daily work routine then a startup may not be right for you. Startup employees often end up having to play multiple roles within the business and have to shift back and forth between those roles on any given day.

You think you will get rich

Being an early-stage employee of a startup can have its benefits. I’ll talk about that below. There are plenty of stories of newly minted millionaires that Microsoft and Apple created out of their early employee pool. Keep in mind that means that you have to work for a very successful startup that beats the odds.

Also, from a salary perspective, startups don’t always pay market rates to their employees. Instead they try to compensate them in other ways. So, don’t expect your salary to be what you might earn at a large corporation.

You need a set schedule

Similar to needing structure, if you are the type of professional that wants to be able to clock in at 8am and clock out by 5pm then a startup isn’t right for you. Startups are notorious for their founders and employees pulling all-nighters to deploy their latest software release.

You need corporate-level benefits

Startups aren’t always able to offer competitive benefits. Take health insurance as an example. The more employees a company has the more likely it is to have less expensive health insurance premiums. When an insurer is spreading the costs of health insurance across five employees they aren’t as likely to be able to keep the costs down.

Reasons you should work at a startup

While working at a startup can be challenging, it can also be a great experience. Here are a few reasons you might want to consider joining a startup.

Broad experience

Since you may end up wearing multiple hats working at startup you are likely to gain broad experience in a lot of areas. When you work for an existing corporation you often times perform one role and aren’t exposed to other areas of the business. For example, if you are in Marketing you might not be involved in the financial planning aspects of the business. But as a startup employee you are more likely to gain experience in a lot of aspects of the business.

It can be exciting

Working at a startup can be very exciting! Especially if the startup is creating a groundbreaking product or service that will change the world.


I have worked at corporations before where I was afforded plenty of flexibility in my schedule. By more often than not companies expect you to work a typical 8am-5pm shift. Whereas many startups offer flex schedules as a perk of the job. If you are a developer and want to work 5pm to midnight, no problem. Want to work from your local coffee shop for the day? Go for it. Startups tend to give their employees a bit more flexibility. After all, they were the original remote work force.

You like a less formal environment

Startups tend to have less formal environment. Particularly when there are fewer employees. So called “open door policies” aren’t as common at a big corporation. But in a startup it isn’t uncommon to just walk into the CEO’s office and make a decision right there on the spot. Startups are usually less formal when thinking about work attire and office settings.

Should I work at a startup? How to decide

The key is understanding the type of professional you are, the things that matter to you as a professional, and the environment where you work the best. Deciding to work for a startup for the wrong reasons can be a mistake. Be sure to take the time to consider all things that mean the most to you.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store