Leap of Faith: When to Quit a Great Job to Start Your Own Company

Reid Hoffman famously said “You jump off a cliff and you assemble an airplane on the way down” in the context of starting a company. Excellent analogy.

However, it would be plain stupid to jump off that cliff without preparing well, carefully considering the best time to jump, and be equipped with minimum viable skills and resources to assemble the airplane. Exactly the same applies when deciding to take the leap of faith and start a new company.

Few months ago, I took the jump. After careful consideration, I concluded it was the right time for me to make the transition back to my entrepreneurial roots. I left a great career and an awesome team of friends and mentors at LinkedIn to start my new venture, Travelade.

Having been involved with the startup and tech scene in Silicon Valley and Iceland for over a decade, I know many entrepreneurs struggle with this decision of when and if to leave a great job to start something on their own — or the opposite, just jump without too much thinking.

Here’s my personal take on what matters most in making this decision.

Make Sure It’s Really What You Want To Do
A great entrepreneur and mentor of mine, Ryan Roslansky VP of Global Consumer Products at LinkedIn, asked me an excellent question when I told him I was leaving LinkedIn. He asked if I was running to something or running away from something. Spot on. If you’re considering leaving your current job, ask yourself if you are running away from your current career — or if you are running towards an opportunity you feel extremely passionate about. Start your company if you are running towards something.

Understand Your Own Motivation
Not only do you need to be certain that you’re running towards something, you also should have an understanding of why you are excited about the journey. Being honest about your own drivers and motivations helps you make better decision — both about starting a company as well as ongoing decision while building it. People have different drivers and end-goals for doing a startup and there’s no right answer. It’s about knowing yourself (and your co-founders) well. Ask yourself if you are in it for the money, for impact, for autonomy, for personal or professional growth or anything else. Here’s a great article for further reading on why to start a company by Hjalli, Founder of DataMarket (acquired by Qlik).

Build a Support-Network
Seeing your company succeed and have a positive impact on others is incredibly rewarding. However, it takes resilience to get there. You also go through grueling times when you’re on the verge of giving up. Like many times. A strong support network can up your chances of getting through those times (and save your mental health). First and foremost, do your spouse and your loved ones back you 110 percent? Do you have a network of friends, other entrepreneurs and mentors who can give you feedback and support when needed? Do you have someone you can trust with the truth of how shitty things are really going the same day as the media is praising you for how well it’s going? Personally, I would not do a startup again unless being confident in having a super-tight support network.

Take Calculated Risks
Last but not least. Do your homework: Research the industry and competitors, talk to industry-veterans, potential users, and others who have failed in the space before. Try to test your core hypotheses, start building a prototype. I could go on and on. Simply put, try to go as far as you can before you make the jump (assembling that airplane will be easier if you have a draft-blueprint and some components stitched together already). Just remember to also make an effort to be your own devil’s advocate in order to avoid confirmation bias. Doing your homework properly is not about guaranteeing success, it’s about taking calculated risks and being okay with it.

While everyone’s situation is unique, I hope these thoughts based on my personal experience can be of guidance to all entrepreneurs out there looking to make the jump. Quitting a great job to start a company is (almost) always a tough decision. It requires a leap of faith, just like jumping out of an airplane.