An Idle Mind is the Devil's Workshop

My wife commented to me yesterday that I always seem glum at Christmas. At first, I thought, huh, really? But then I realised it's probably true. Come Christmas every year I get the shits on. Why though? Christmas doesn't hold any particular meaning for me (other than getting some time with family) so it's not the Yuletide spirit. I'm not generally the brooding type, so it's unlike me to be like this...especially at Christmas. So what gives?

Well, as a startup founder, I'm generally pretty busy most of the time (although I admit this year I haven't been as busy as others). I rarely take time off work, and when I do, we're straight on a plane and off travelling someplace. So the Summer break is the one time of the year where I find myself with nowhere to be and nothing much to do. An idle mind is the Devil's workshop.

It's at the end of the year that I tend to take stock of what I have and haven't achieved in the previous year. I'm generally disappointed. I look back and look at all the things we said we'd achieve this year, and ask myself why we didn't achieve them? Did I not work hard enough? Did I make bad decisions? What could I have done better? Often the answer is that we did everything right, and yet things still didn't work out. Sometimes we do everything wrong, but we still have a good outcome! Go figure!

This year has honestly been a clusterfuck of monumental proportions. Yet, at the end of it, I think we're still in a better place than we were 12 months ago (there'll be a blog post on that soon). Related: the book 'Antifragile' is a terrible read (but I highly recommend it).

So what did I do this year? Well, the clusterfuck started because last year I finished up at BugHerd (a business I spent 6 years building), so this year was all about finding out "what's next?"

  • I started 2017 making a game with two exceptionally talented friends (a writer and an artist). I quickly found that I suck at making games. It was great fun learning new stuff, but it wasn't really making use of the skills I already did have.
  • So I poured myself into being a Startmate mentor/partner for the Sydney 2017 batch. I loved doing it, but unfortunately, volunteer gigs don't pay the rent! 
  • During this time I'd been working with 500 Startups helping them set up shop here in Melbourne. I had hoped that I'd be the one to lead the Melbourne program, but sadly for me, that honour went to Rachel Neumann (and well deserved). Of course, in the end, I was glad I missed out.  
  • I then took some early steps into starting a small angel fund with a good friend. I spent about 6 weeks researching, listening, talking, learning before coming to the conclusion that I am not (and probably never will be) a suitable candidate for a GP role. I hate raising money, I hate making deals and I hate paperwork. There's no way I'd do it for a living! 
  • Somewhere in there, I had another (failed) attempt at writing a book.
  • Startmate Melbourne came along, and so I jumped back in head first and once again discovered, whilst fun, it won't pay the rent. I guess I should've paid more attention the first time! 
  • Around this time we completed the investor buyback of BugHerd from our investors, and shortly thereafter I came back to being CEO again (yes, I said there'll be a blog post). It was a nightmare 18 months but was a relief to get it done (with many thanks to Tom Pisel).
  • In September I was supposed to mentor another accelerator program.. but by that stage, I was so totally burnt out from anything to do with startups/community/money/investors and just couldn't do it (sorry Scott). 
  • Oh...and in amongst that, we built a house, rented a house, sold a house, moved house twice, got kids started at a new school all while my wife and I were both mostly working/consulting full time.

So whilst it's tempting to sit back and think I didn't achieve anything this year, I did learn a bunch. I learned I'm not going to earn a living making games or being a novelist, I'm definitely not going to raise a fund and despite my best efforts, I'm not going to work for (and certainly not run) an accelerator. 

But I also learned that 2 years after I was forced to fire a bunch of people they're still happy to hang out with me (even if I have to bribe them with Star Wars tickets). I learned that whilst I'm a bit rusty, I can still actually code. I also learned that there are people out there who want to work with me, follow me and invest in me. I learned that you can either create the world you want to live in or invest in someone else's; and that the latter doesn't excite me all that much. I learned that just because you can, doesn't mean you should and as a result, I learned to say no.

I re-learned that what we do is really fucking hard and that I shouldn't be so down on myself for not "smashing it" (and nor should you be if you're also not smashing it). I re-learned that our "shitty little web app" was actually pretty successful (providing you're not a VC trying to raise another fund). I re-learned that what's good for a VC is not always what's good for a founder (and vice versa), and that, as a result, many startups should just never ever take money from a VC. 

Here I am at the end of 2017, mostly back where I was at the end of 2016. A little bit older, but a lot wiser (and a whole lot greyer). I sold a biz, started a biz, bought back a biz and at the end of it all, learned a whole lot about myself. That's not such a bad outcome.

So why does all this make me grumpy at Christmas? Whilst I'm certainly grateful for what I have, and what I've achieved, I'm never satisfied. Every year I look back and think, "ok, what's next". I wonder what I can double down on next year. What didn't I do, that I should be doing? What did I do that I shouldn't be? What can I do better? The answer is, of course, a lot.

4 responses
Maybe happiness is more likely to come from acceptance of yourself as you are, than from measuring whether you’ve improved between two arbitrary dates. You’re awesome. You’re the wisest guy in startups I know south of the Albury-Wodonga Line. You’re funny af. You are good to people, run a tight family, and you can code! Measure resilience: shy of SkyNet emerging there’s really nothing that would prevent you from providing for yourself and your family in top 10% of first-world quality of life while allowing enough time to be a dad and husband. You may be unemployable but you’re also un-unemployment-able. You’re not on the journey towards being successful enough. You’re successful enough.
The curse of the overachiever - I can relate. Nice work dodging the 500 Startups bullet, and I'm happy to hear you're back in the captain's chair with Bugherd. I'll be keeping an eye out to hear the rest of that story!
You've been an amazing mentor Alan. (Comments Alan is also quite helpful).
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