48: When to quit your job and follow your North Star

Whether you’ve got something lined up or you need a fresh start, quitting your job is a huge life decision, — in today’s episode, we’ll cover signs to look out for that might be telling you it’s time to move on from your current role. Being successful and happy in martech requires having a true north for your career.

Sometimes, that means recognizing that your current workplace isn’t helping you advance your career. It could be you’re not happy with your work culture or work for a bad manager; or, it could be that it’s time to move on to acquire the skills needed to reach the next level.

Alright JT, I feel like this episode has been a long time in the making. We teased about it in the trailer, it’s something most people do a few times in their career; handing in that two weeks notice.

But leaving a job isn’t always about leaving a bad workplace or boss. Sometimes you work for someone awesome at a great company, but it’s time to move on for your own progress.

No one gets to decide that for you. You call the shots in your career. 

Leaving a job should be objective: Make a list of pros and cons when comparing two positions.

What factors matter most to you? What are your goals? 

Knowing when to quit your job is about having a sense of your north star for your career.

Having a north star for your career

  • Freedom with your career
  • Have red lines
  • Career mission statement 

For me, there’s many ways you can make this more complex for this but in its simplest form, the north star of your career is your vision for fulfilling 3 things:

1- Passion and meaning, something that motivates and energizes you
2- Sustainable income, cover costs comfortably, save for future
And 3- can be pursued in balance with your personal life, something that allows you to spend time with family, build strong relationships and good health. 

That’s it, it’s a simple formula. It’s more guide posts. 

Early in your career, the 2nd factor is less important and usually the 3rd factor is less busy so you can double down on the first factor and discover your work passion and meaning.

It’s okay to change your North star 

Career plans are meant to be flexible. My favorite part about the north star metaphor for career purposes is that the North star actually changes and it isn’t exactly north.  

The current north star is Polaris, but because the Earth’s axis shifts every several thousand years, different stars will serve as north stars. 

But also, the North Star isn’t exactly north. Polaris is the closest star to true north, and is “close enough” for most basic navigation purposes. So your career north Star can change and it doesn’t have to be super specific.  

Like our sailing ancestors, when we are lost at sea, it’s meant to guide us. We can always look up to the sky to reorient ourselves and get back on course.  

Example: Years 1-5, no salary objective. Only objective: trying shit out.

Years 4-6, company objective; work with top talent in cityYears 5-7, find a niche or dive into leadership


Advice: Have specific career goals every year or two, reset them. Maybe you joined a company as a marketing specialist with the goal of learning everything you can about their tech stack to one day become a marketing automation manager. That could be with that company, or another.

  • Tell your boss about your goals, help them help you
  • Never say no to a coffee, especially early on
  • Moonlight/freelance
  • Keep a solid LinkedIn profile, keep an eye on jobs

What does it mean to ‘hit’ your ceiling

What does it mean to hit your ceiling and how do you know you’ve hit it? Is it when you staying in your comfort zone too often. “I learned everything I could” but did you? Is that even possible?

Your career needs new stimuli:

  • Growth requires stimulation. If you’re not getting enough in your current environment, it can feel like you’re stalling out
  • No mentor at your current workplace. This is why you sometimes see a chain reaction when a senior leader leaves 

Signs it’s time to quit

At what point did you realize it was time to quit? What are the sure signs it’s time to leave a job?

  • Unsupportive coworkers / boss, when your boss/coworker doesn’t like you.
  • When you hate going to work, get the Sunday scaries.
  • When you bring that stress home. You feel unhappy at home because of work. When it impacts your health.
  • Your role no longer supports your long-term career ambitions
  • You want to work with a different industry
  • You want to work with a mentor or a team that can level you up
  • You just “feel” it’s time for a change
  • You found an exciting opportunity

Career or role switch

  • Sometimes, you just can’t get the opportunity at your current company.
  • If your dream is to be an Marketing Analytics pro, but your company doesn’t invest in the tools you want to advance your career

How to quit your job

  • This is an unsung part of the process. I think that leaving in a respectful manner is incredibly important, and sometimes it’s hard, especially if you’re emotionally invested in the company (negatively or positively)
  • You can determine exactly how but in my mind, it’s definitely worth tying up loose ends and leaving your company in a good position. Aim to leave the company in a better position than you found it.
  • For example, I left Klipfolio on good terms — and I didn’t leave because I hated my job. I left because I felt it was time to learn from others and work as a consultant. A few years later, I found myself back with the team in a more senior role. This opportunity wouldn’t happen if you burn bridges.


You heard it here first folks, 

  • You can’t stay at a job to make others happy, your career is yours to control
  • Leaving a job isn’t always about leaving a bad workplace or boss
  • Sometimes it’s time to move on for your own progress

So what’s your north star? 

Intro music by Wowa via Unminus
Cover art created with help via Undraw

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