How To Decide If You Want to Work In a Startup (or Stay Corporate)

DeathtoStock_NotStock5 How To Decide If You Want to Work In a Startup (or Stay Corporate)

Many of us have been there. Tired of the boring job at a large company, resigned to being ten levels under management with no room to grow, running in place, not growing as a human being. We start to daydream - what if I was a Startup Guy or Startup Girl?

Immediately, we think of airy lofts and open floor plans, tons of snacks, open vacation, equity, being buddy-buddy with the founders, helping build an awesome product that will change the world, etc. We talk to friends who work at startups and they seem so driven and excited all the time. I want my freedom! Screw this corporate crap!

Now, back to earth. Just like in any other company, a startup job can be amazingly rewarding - or pure hell.

Here's what to look for when you think of jumping to a startup:

1) How do you look at risk? Is it excitement for you or a heart attack? Are you gung-ho about new challenges and run with them and own the problem or are you used to doing what you're told?

Frankly, can you survive if suddenly, the company goes under or the job doesn't work out? What if your job description changes drastically? How flexible are you to go get coffee/donuts, even if you're high in management? If suddenly the founders need to pivot or to cut the workforce, it could be a sudden shock.

If you're ok financially and otherwise with this scenario, then it could be for you. Don't take the startup gig it if you can't take the sudden changes in direction, moving quickly, daily shifts in mood and job description. 

2) How do you work? Are you methodical and thorough, harping on every detail to perfection? Then stay away.

Or are you of the 80/20 mindset, focusing on things of greatest impact first and then the rest? This might be for you.

Do you take ownership or do you always defer to others? If it's the first, then you might be a Startup Guy or Girl.

3) What is your learning style? Do you learn best by doing or through books and manuals and specialized trainings? A startup job will often have you doing things well outside of your comfort zone (what you learned in college, what you did in previous jobs, etc.) If learning things by doing is your forte, working for a startup might just be the thing for you.

4) What sort of people push you toward doing your best work? If you're not used to Type A, crazy people cracking whips around you, you will not enjoy it. Startups are different, but their founders tend toward having a very strong vision and a mission. If you're not in line, then often, you'll be yelled at, overruled or sidelined.

5) How stable is the company, especially its finances? Have the founders built companies previously? Have they worked successfully as a team before? How much does the company have in the bank (runway/burn) to achieve its mission and how well is this money being managed?

6) How do you get along with the founder(s) and the team you would work with? Make sure to take the beer test, ask detailed questions and OBSERVE their behavior, above all. If you don't like how people treat each other or how they react to stress (ask!) or other aspects of the culture, then it will wear you down and burn you out. Is the startup full of mature adults or a bunch of bros? It often depends on your function. FInance will be quite conservative and experienced people, whereas the Product Team and Devs will often be 20-something hipsters or bros. Know with which teams and people you would be working and make sure to meet them and estimate how well you can work with them.

7) Where can you grow in your role? Up or out? Don't settle for vague answers from founders. If you're a Product Manager, you will want to grow into a Director of Product Management, for example. If you're an account manager, you may want to become a Sales Director down the line. Be clear in where you want to go and that the founders and management know it and are on board with helping you reach your goals.

8) What is the company's mission and how closely aligned with it is the vision and the execution? Why do you want to work for a startup? Is it because you identify with the mission or because you're after the equity? Don't be seduced by wanting to "change the world" or the Perk Trap or "moving fast and breaking shit."

The work is often insanely hard and the hours beyond crazy. Equity almost always vests after a year and even then may not be worth anything. Too many free snacks make you fat and sick. You can't actually take as much vacation as you want (you'll be fired immediately when you try). Most of what you do will not come close to changing the world. You may want to move fast and break stuff, but there are always constraints like money and hours in the day and personality conflicts.

9) How happy will you be just to lay out your everything on the line for the company and learn as much as you can and work with super-smart people on an important problem (unless you're building yet another video or chat app) and then walk away? In the end, this is by far the greatest benefit, unless you actually build something world-changing, your equity actually vests and is actually worth something.

10) Does your family situation give you breathing room to work for a startup? If you're a single, urban 20-something, you have little to lose except sleep and hair and life enjoyment. You'll be fine. If you have a family and commitments, then it may not be the best bet to work for a startup, given the insane hours and constant stress and often unpredictable schedule. It takes a toll on you because you live your job (or you lose it).

In the end, there is no magic formula for whether it makes sense for you to take the plunge. An overwhelming number of startups fail each year. Nobody but you can decide what lifestyle you want or what skills you want to learn, with what people to work or what your mission in life is.

That said, if you are lucky to find a startup job that aligns with your mission and values and gets you in the door, working with amazingly smart people on an important problem with money and a great team behind you, ABSOLUTELY GO FOR IT!

Your life will never be the same and despite the hellish stress, it will open a wealth of opportunities for you. Just know, the startup journey ain't for the faint of heart.

Are there other factors you've found important in deciding whether to jump to a startup? Tell us in the Comments below. We would love to hear from you.

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Yuri Kruman is a Healthcare Product Manager, published author, blogger at BlueprintToThrive.com and health tech entrepreneur based in New York.

*The views expressed herein are his own*