43 questions to check if you can be a lifestyle entrepreneur or digital nomad

See that photo up there? It’s BS by the way. Tried and tested, and it only got my eyes freaking tired, with sand into laptop while my ass heats up to cook my balls.

When people know about our travels (Debbie and I try to do 90 days of travel a year, minimum 60), they always envy our lifestyle, and ask us how we did it.

Frankly, the how-we-did-it question is not even close to the real question they should be asking, which is:

What are you getting into?

And truth be told, there’s nothing much to envy about, which is why we hardly share our check-ins and travels on social media. Unless it’s something too stupidly funny. 🙂

Inspired by a post by Marcus Teoh, Debbie and I decided to compile a list of questions that should help you decide if being a lifestyle entrepreneur or digital nomad is something you really should strive for.

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How to Battle the Green Monster of Entrepreneurship

There are only a couple of green monsters out there. It’s not the Hulk, or how your private parts looked like after being stung by an exotically fatal jungle hornet*.

No, I’m talking about the one inside you (again, dude, not the one in your pants).

Yeah, let’s talk about jealousy.

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What this local startup did after pissing me off

This all happened within a month, and I thought in the spirit of Fuckupnights, we can all learn from the incident.

Who’s the startup you ask? Piktochart.

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The Making of Desperate Entrepreneurs

Bet you’ve seen or worse, worked with one. These special breed of entrepreneurs, or for the lucky ones, is just a temporary phase, usually portray one or more of the symptoms below:

  • Change company direction every 3 days
  • Change team member’s and staff’s roles every 3.5 days
  • Quote Sir Richard Branson and his 500+ companies
  • Use the term pivot too often
  • Do the “pivot” lagi more often
  • Jack of all trades but master of none
  • 5 years later at the school reunion, he’s still working on that idea/startup with no apparent growth (his mom secretly texts you to help “advice” his son)

If entrepreneurship is a mix bag of many skills, traits and mojo, then the equation for desperate entrepreneurs are:

Desperate Entrepreneurs = Balls of Fire + Balls on Fire + Tons of Unpaid Bills + That One I Also Can Ao + Slap-Worthy Ego - FOCUS

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Doing Entrepreneurship Mythbuster-style

Three years of doing KICKSTART, where we gather about 250 entrepreneurs once a month to network and learn from mentors, and personally running a few businesses (failed four at least) for 12 years, you wanna know the truth? I get kinda icky feeling when I’m called an entrepreneur.

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Hacking Emails & Events, and rock the shit out of ’em

Ok, let me just say that this presentation at the 1AES Growth Hack Labs was no way for me dicking-off, showing the wizardry I have around events and email writing. Just that over the past few years of running KICKSTART.MY, FuckUpNights KL and other various workshop, creative email copywriting accounts to over 83% in the success of filling up those events. In this workshop I’ve shared stuff that has worked for me, cutting-off the BS around email and events marketing, and basically, yeah, dicking-off lar. 🙂

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Entrepreneurship Development, Education System. Same same lar…

Ok, this is gonna be a piece that may be hurtful to some. So if you’re sensitive like some country leaders who’s ideal political practice is to remove anyone who say/write/update FB with things they don’t like, then better go back to scrolling that semi-hypnotic FB timeline for the 85th time today.

Ready? Here goes.

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What are startups running from?

At the end of this blog post, I predict that two things will happen. And if you’re the smart ass who thinks, “Better scroll to the end now and read them predictions!”, then I’ll predict something else.

You’ll scroll back up here again.

Yup, welcome back.

Here’s the thing. Over the few years, I have to admit that the number of “startup entrepreneurs” are increasing, and initially, I felt proud. You see, when I started doing this glamour thing called entrepreneurship over a decade ago, hardly would I meet people my age. (Yeah, one of the reasons why we started KICKSTART back then was because I’m tired to seeing entrepreneurs my dad’s age at networking events. They so love to wear those ties and suits.) But now, I do. May it be at an event at an awesome hall, a meetup at the top floor of a tall building or at a workshop deep in the hearts of Cyberjaya, I see youngsters dominating the crowd, and that made me feel happy.

For a while. Until you deep dive a bit.

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Let’s talk about your Bankable Skills.

IMG-20150713-WA0001After a killer breakfast in the busy corner of Seminyak, Bali (seriously, the place is called Corner House because, well, it’s around the corner), I’m faced with a life-changing crossroad – do I nap, work, or write something? After (pretend) working for like 3 hours, I decided to shift place and shift gears. I moved upstairs and do this writing shit.

One (coaching) question I recently liked to ask aspiring entrepreneurs or wantrepreneurs is:

What are your bankable skills?

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