There’s a simple way to know if you should quit your job. Look at your boss - their role, their salary, their lifestyle, their level of stress, the amount of vacation days they take, their family life, their health - and decide if that’s exactly what you want your life to look like.

Because it’s unlikely your life will look much different than theirs if you get that role.

It’s tempting to look at parts of that person’s life and think they’d make you happy - maybe the salary is great and there’s prestige in the title - but those come with everything else on the list. If you don’t aspire to live the life your boss is living, you’re probably wasting your time at that job - you can’t get the good without the bad.

The same thing is true for entrepreneurship, though it’s usually harder to find and recognize the people a few steps ahead of you on the ladder.

If you want to raise funding, you should find a handful of companies a few steps ahead of you - similar industry, similar trajectory - roughly where you think you’d like to be in 2-3 years, and see if that’s the type of company you’d like to run. If that founder’s life is the one you’d like to be living.

Expert Interviews are wildly helpful here - build a process to speak with entrepreneurs running the types of companies you’d like to run. Surround yourself with the type of people you’d like to become.

This is easy to say and hard to do, so I’d start with low hanging fruit. Make a list of companies you think are the best example of the type of company you’d like to build. Certainly reach out to all the founders, but also see if they’ve been guests on podcasts or if they write blogs. See if you know any employees at those companies or have any second degree connections you can get introduced to.

It’s a bit of work, but it’s a great idea to see if the life you’re hurtling towards is one you’d actually like to live.