7 Questions To Ask Yourself Before Leaving Your Corporate Job For A Startup

You’ve been in your corporate career for some time now and are craving a change — something more dynamic, less siloed, and with the flashier benefits befitting of today’s job market. 

Ultimately, you’re finding yourself wondering: Should I work at a startup?

Taking a C-suite or another senior-level role at a startup has its perks, but there are just as many cons to consider. 

Yes, there’s the energy and excitement of building something new that’s espoused by many a startup culture. 

But working for one comes with its share of risk; three out of every four startups fail, according to the Wall Street Journal, and as a senior leader, you’re going to have more skin in the game. 

Plus, some of those flashy benefits, like unlimited PTO, may mean less to you personally than, say, your current corporate gig’s 401(k) matching. 

Even still, there are several good reasons to make the switch to a startup. 

If you’re interviewing with a startup whose mission excites you, ask yourself these seven questions before taking the job, according to the experts we heard from. That way, you can be sure you’re making a move to a startup from a clear-headed and grounded place.

1.“Am I mentally ready for a potentially much higher workload?”

“Starting or joining a startup is most likely going to take a toll on you, both mentally, time-wise, and financially,” Anton Söderström, Founder of Dagensfokus.se, said. “It’s crucial to make sure that you are ready for this type of change. Startups are rarely the heaven-like experience that people make them up to be. Rather, it’s a heavy investment that a lot of people are not mentally ready for.”

2.“What do I know about this startup’s investors?”

“Who is the team behind this business? Investors invest in people, and so do we as entrepreneurs when we decide to put all our chips in a pile,” Ross Kernez, a digital marketing mentor to startups, said. “So make sure you completely believe in your team before jumping the fence. Do your own due diligence and make sure you know everything about them.”

3.“Am I running towards something or away from something?”

“Are you chasing your ambition or avoiding the things you don’t want in your life — a horrible boss, a negative business culture, too much stress, or a lack of work-life balance?” Andrei Kurtuy, Co-founder & CCO of Novorésumé, said. “You’ll have to be tenacious! There can’t be any doubt in your mind about what you’re after.”

Similarly, entrepreneur Chad Price recommended asking yourself: “Is this what I truly want?”

“Do you feel you are obligated to hop on this position, or are you so desperate to leave your current job that you’re taking whatever comes to you?” he said. “Take a step back to make sure that you really are interested in the position because you want it and not because you need it.”

4.“Can I be comfortable with ambiguity?”

“I believe that when you transition from corporate to startup life, you leave behind a world of predictability and knowingly enter a potentially volatile environment,” Joe Manna, Content Manager of Alyce, said. “Plans are subject to change. The market rebalances. To thrive, you must be the type of person who is energized by the possibilities presented by change. A project you’re working on one day may be abandoned or modified the next due to shifting priorities.”

By definition, as Manna put it, startups are “about change.” Because of that, you must “have the courage and agility to embrace ambiguity when it occurs,” he added.

5.“Does this startup have the appropriate funding?”

“At the very least, they’re looking for and targeting the correct investors rather than ‘random’ cash,” Corey Tyner, Founder of Buy Yo Dirt, said. “When examining the company’s longevity and support, it’s critical to know who the investors are and what they’ve done in the past. You can have a strong brand or product, but if the CEO and product are not aligned with investor expectations, the firm will have a difficult time matching mismatched expectations in the future.”

6.“Am I ready to get my hands dirty, finding new ways to be productive while using fewer resources?”

“Large corporations have more money to spend, and as a result, additional resources are available to address issues, such as employing external agencies to assist scale and executing creative campaigns,” Sara Johansson, Customer Success Manager at Onsiter, said. “When you’re working for a startup, you have to be extremely careful and efficient with your spending. To be productive, you must be willing to use ingenuity to solve issues rather than having an excess of resources.”

Startup life, Johansson added, isn’t for you if “you don’t want to get your hands filthy and do the work yourself.”

7.“Am I comfortable with taking on a new role that’s essentially undefined?”

“When joining a startup, you may be applying for a specific position, but it is likely that sooner or later your responsibilities will expand,” Tina Hawk, SVP of Human Resources at GoodHire, said. “Startups naturally involve a much greater degree of uncertainty and blending, especially in executive roles.”

If you’ve been accustomed to working only jobs that come with extremely clear duties and a yet-clearer ladder for advancement, it’s time to get real with yourself about what scrapping both could mean for you. 

“Asking yourself honestly if you’re comfortable with that lack of definition is important,” Hawk said. “You can also look carefully back upon your career to date in order to get a clearer picture of how well you tend to handle undefined or blended roles.”

Find more advice about job searching with a career transition in mind on the blog.