Ask Doist: I Like My Job But My Company Doesn’t Offer A Lot in the Way of Career Growth

A remote worker wants to know if he should keep his fluid role in a flat company or pursue more traditional advancement

Remote Career Growth Banner Margarida
Illustration by Margarida Mouta
Ask Doist is a regular column answering real readers’ questions about work and life, from the philosophical to the practical. Got a question? Email us at

I am a remote worker since 2010 and have found your advice very helpful. What I am missing right now is advice on how to progress my career. My company is fully remote, the hierarchy kept to a minimum, and the roles somewhat fluid, which makes me wonder how I can advance my career. Right now I feel my growth is strictly related to the company’s growth. Do I need to become the CEO 🤔?  Do I need to change company?  Or are there processes I can suggest internally to improve the situation? Thanks!

I can definitely relate to your situation: I’ve been working at Doist for 6 years. We’re a fully remote company, the organization is relatively flat (just CEO, CTO, and COO at the top then team heads then everyone else), and roles are somewhat fluid, though that’s changed as we’ve grown. I don’t think I even have an official title.

I’ve come to see both the advantages and disadvantages of this kind of work environment.

The pros:

  • Fewer layers of bosses usually mean you have more ability to make and/or influence decisions.
  • You tend to have more autonomy and ownership over your work.
  • Fluid roles mean you have much more freedom to define your own path around what you want to do and learn.

The cons:

  • Fewer opportunities to manage people, if that’s the way you want your career to go.
  • You can’t “climb the ladder” in terms of levels and titles because there are none.
  • Typically, there’s no one at the company who’s done your job before, so you have to be more proactive in identifying areas of growth and finding ways to pursue them.
  • You may have to seek out mentors outside of the company rather than in it.
The way people think about “career growth” is changing and becoming much more inclusive of different paths.

Luckily, the way people think about “career growth” is changing and becoming much more inclusive of different paths. Moving your way up a ladder from one set title to the next – from doing the work to managing the people doing the work – is just one way to grow your career. More and more companies are creating individual contributor tracks for advancement so people who are great at their jobs aren’t forced into management in order to grow their careers (and paychecks). In her book Lean In, Sheryl Sandberg famously described her career as more of a “jungle gym” than a ladder:

Ladders are limiting. Jungle gyms offer more creative exploration. There are many ways to get to the top of a jungle gym. The ability to forge a unique path with occasional dips, detours and even dead ends presents a better chance for fulfillment.

While a more senior title on your resume can be helpful when making a move to a new company, the narrative you can tell about your work, growth, and impact in your previous roles is much more important, especially if you’re in the tech startup world.

I think these are more important questions to answer for yourself in deciding whether to move on:

  • Do you feel like you’re still personally growing in your role?
  • Are you still challenged?
  • Are those the challenges you want to be taking on?
  • Are you learning new things?
  • Are those the things you want to be learning?
  • Do you feel supported and challenged by your boss and coworkers?

If you answered yes to those questions but a manager role and title is really important to you, is the company growing? They may just not have gotten to the point where adding more levels makes sense.

Talk to your manager about the things you’re thinking about. If they’re good at their job, they’ll help you find ways to grow. If they’re not, maybe it’s time to find a new job with a manager who will. Either way, it will become clear whether the company’s trajectory and where you want to go personally are matching up.

There are lots of valid reasons to want more traditional career advancement. If that’s the path you decide to pursue, it sounds like you should find a company that better aligns with your goals. Just be sure it’s what you really want for your career and not just what society’s told you your career should look like.

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