Learning When To Quit Your Job

I wouldn’t have made VP of Sales before 30 without quitting great jobs.

However, quitting great jobs is also how you can still be an SDR at 65.

There are five things you can ask for in any job:

1. Do you love your team?
2. Are you learning?
3. Do you love your work?
4. Are you accelerating your career?
5. Are you earning?

Let's break down what you should focus on throughout the different stages of your career.

Early in your career

Focus on putting yourself in hyper-dense clusters of brilliant people & learn everything you can.

By immersing yourself with highly talented, skilled, & motivated individuals, you'll gain access to a wealth of knowledge that can significantly accelerate your learning curve.

Find a supportive community that encourages you to gain the skills that will set you up for the next stage of your career. Absorb their wisdom, adapt to their standards, and learn how to solve problems - just like they do.

I know folks who have found themselves in these environments just via cold email. In fact, I still work with people today who simply reached out to me.

Don't let the "what-if" get in the way of your own career.

As you approach the next stage, you should have acquired 2 things: A robust skillset & an initial network, which will be pivotal in the next stage.

Mid-stage of your career

Focus on finding a job you love and accelerating your career.

By having some actual skills, you can now pick opportunities that allow you to do more of the work you love.

Instead of white-knuckling your way through work, find what fuels you to come back the next day at 110%. Harnessing your intrinsic motivation will only make you better at the job you’re already crushing.

And by building an initial network, people will refer you to career-accelerating opportunities because you’re so damn good at your job.

Late-stage of your career

Focus on your earning potential.

I took a pay cut to be the Head of SDR at Carta, but I knew it was an opportunity to become a Director of Sales over staying as an AE.

Strategically seek positions that accelerate you to your end goal, there's often a faster way up the ladder than growing within your role

Think long-term & identify your end goal, then work backwards to understand the early/mid-career roles that will set you up for that position. The interim roles may not pay the most in the short term but increase your earning potential in the long run.

Pave couldn’t pay me what a Series F startup could, but that led to me becoming a VP of Sales instead of climbing the ladder slowly at a later-stage company.

Do the job you want & showcase your upside in your current role. By the time your prospective employer is considering you for the position, it should already be a no-brainer.

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Every time you switch jobs, two things happen.

1. You re-roll the dice in every other category
2. You restart the internal capital-building process

Make sure you’re rolling the dice on the RIGHT THINGS for the stage of your career.