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The Downsides of Working for Yourself (Ep. 8)

There are quite a few benefits to working for yourself. For many people, entrepreneurship is the dream. But it’s not perfect — it comes with a few downsides to balance out the upsides. So we decided to talk about a few of the potentially surprising downsides we’ve noticed. Even if you don’t work for yourself, some of these apply to working autonomously in general, which a lot more of us get to experience while working from home this year.

Things mentioned in this episode:

This week’s episode is sponsored by:

  • Skillshare: With thousands of courses in a wide range of different skills, Skillshare can help you take things to the next level. You can also get started with a free trial with unlimited learning (including Thomas’ productivity and habit-building classes!) at
  • Brilliant: Accelerate your learning in math, science, and computer science. Start learning for free at — and if you’re one of the first 200 people to use this link, you’ll also get 20% off your subscription.

Other things we mentioned in this episode:

Want more cool stuff? You can find all sorts of great tools at my Resources page.


  • 0:00:00 – Intro
  • 0:02:10 – What we’ve been up to
  • 0:11:18 – Working on your own
  • 0:13:05 – Managing your time and energy
  • 0:20:34 – Making yourself stop working
  • 0:25:39 – Sponsor: Skillshare (Learning new skills)
  • 0:28:16 – Sponsor: Brilliant (Learning problem-solving skills)
  • 0:29:44 – Working too many roles
  • 0:35:40 – Building relationships
  • 0:39:39 – Feeling like you’re not doing enough
  • 0:44:44 – Being self-disciplined and delegating work
  • 0:53:03 – Favorite animated shows
  • 0:58:13 – How do we organize our books
  • 1:02:14 – Conclusion

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