TMBA 395: Should You Quit Full-Time Entrepreneurship?

TMBA395: Should You Quit Full-Time Entrepreneurship? post image

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One of the dichotomies that Dan and Ian often address on this show is the difference between being an entrepreneur and having a job.

Today’s podcast is going to cover a rather taboo subject in some entrepreneurial circles: making the decision to stop being an entrepreneur and go back to the daily grind of a 9-to-5.

Anna Wickham is a former TropicalMBA intern, who traveled the world for nearly ten years and eventually started her own marketing agency.

Over the last year or so Anna has been feeling the pressure to remain an entrepreneur, even though she was questioning whether it was really the best fit for her.

In this episode, Anna opens up to share her fears and hesitations about the entrepreneurial life, and why she ultimately decided that it wasn’t healthy for her to keep pursuing it full time.


Listen to this week’s show and learn:

  • What made Anna originally decide that she wanted to live a nomadic lifestyle. (7:05)
  • The struggles that Anna faced in growing her agency. (11:35)
  • When Anna started doubting whether she wanted to be an entrepreneur. (13:17)
  • How Anna feels about “resume gaps”. (21:18)
  • Why deciding to get a job doesn’t mean that you aren’t an entrepreneur. (27:25)

Mentioned in the episode:

This week’s sponsor:

A big thanks to Growth Ninja – this episode’s sponsor. Are you looking for a reliable and hands-off way to scale your company’s revenue? Growth Ninja is an industry proven Facebook ad service that can explode your sales funnel.

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Thanks for listening to our show! We’ll be back next Thursday morning 8AM EST. Cheers, Dan & Ian

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Published on 06.29.17
  • Kiri Masters

    I had a very strong reaction to the discussion around ‘resume gaps’. This seems like such an antiquated concept and I’m shocked that it’s still a concern for jobseekers who have taken time out of the traditional work force to pursue something (travel, family, vocational calling) which few people could argue is more important than a job. Such a strong reaction that I wrote a medium post about it. Hope it’s OK to share here.

    Thanks for sharing your story Anna. I think its courageous to say publicly that the life you were pursuing didn’t serve you anymore. That is not to say that you were ever wrong.

  • I completely agree with you — the word “antiquated” perfectly describes the concept of the resume gap. Even though I will now be employed in a more traditional sense, I will always own my own life timeline. It’s inconceivable to me to plan my life out of fear of a hiring manager.

    So glad Dan brought up this important topic! Love the article on Medium btw, thank you for sharing as this needs to be talked about more! Thanks for your support, Kiri :)

  • In a similar boat! After our stint at AMZT in China blew up there was a clean slate to start over again, so I moved to NYC to take a stab at the tech/startup space (still interviewing). Don’t think it’s as black and white as many digital nomads think when it comes to the word “job” of going to a 60,000+ soulless company vs being on your own.

    Plenty of startups & smaller tech companies are doing cool stuff like Classpass, Casper, Spotify, etc. that probably wouldn’t be that bad of a place to work and at least you’ll get paid market rates. Even WeWork offices have Bose speakers bolted on to the restroom ceilings so it can’t be that bad :D It certainly beats looking for a cafe that has good internet all the time in SEA.

    Seems like movement between jobs, companies, & founders is quite normal here as things always go boom and bust vs. bootstrapping something for a longer term horizon. Just never realized it since the digital nomad space can become quite an echo chamber :D

  • I remember emailing Dan about this very topic… In the end, I’ve since joined three startups and finally found one (based in New York, I’m heading the Manila team) I would be happy to grow with. I feel like a mini entrepreneur (in terms of skills, relationships, experience, learning, growth) without the emotional and financial roller coaster.

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