97/100: Till You Get Punched in the Face, or 2016 in Review

97/100: Till You Get Punched in the Face, or 2016 in Review

Everyone has a plan till they get punched in the mouth.
— Mike Tyson

Or “till they fall off the bouldering wall and mess up their knee”, in my case.

Yes, friends, this quote I love sums up my sabbatical – and my year – pretty well.

Thus, in this last post of my sabbatical adventure (never mind that it’s the 97th day instead of the 100th, I fudged a week in the middle if you recall, so we’ll just call it even) we’ll also neatly wrap up all of 2016. And what a year it’s been.

First Up, the Sabbatical Review: How I Did

Against the goals that I’d set out, here’s how I fared:

  1. MEGABRAIN: I learned a lot about BCIs over the last few months. My takeaway is that it isn’t an area I can work on directly at this time. The exploration has, however, created a few new opportunities that I’m looking forward to exploring in the coming year – mainly in adjacent areas, including Artificial Intelligence.

  2. DOMOREBOOK: Here’s a project I actually took to sort of completion, and am now going to unceremoniously kill. By this I specifically mean that I’m going to shut off the Shopify store subscription, which I had been using as a payment gateway. Going through the exercise of rapidly creating a (theoretically) sellable concept and its website from scratch was great, but the feedback isn’t there. I made just one “sale” of this book instead of the planned 3, and, ultimately, it doesn’t feel like something I want to pursue. So, I’m ceasing all effort in this area.

  3. WORK: I had a chance to connect with a couple of incredible founders, namely Leo from Buffer and Mike from Zapier, who are building their companies remotely, and are quite a few steps ahead of Postcard. Ultimately, it feels to me that the tradeoffs between co-location and remote are balanced, making them both viable options. The point remains that your team should make this decision deliberately and personally, instead of just following the norm. This is another area where I’m ceasing further exploration.

  4. FITNESS: Frankly, this was one of my favourite areas. I didn’t expect it to be; I’ve long struggled to find something active that I enjoyed enough to do regularly and consistently. Bouldering, augmented with a couple of very short gym workouts in-between, has done incredible things for my body and I’m utterly in love. While I didn’t actually reach my fitness goals, I made tangible progress toward them:
    – I’ve completed more than 6 green problems (one level below the orange I’d been shooting for)
    – At last attempt, I could do 3 consecutive chin-ups (was shooting for 10)
    – Dropped body weight to 129lb (was shooting for 120lb)
    – Dropped body fat to 26.3% (was shooting for 25%)
    – As a bonus, I did a bouldering competition (was shooting for climbing outside)
    Unfortunately, 3 weeks ago I sustained a significant injury to my ACL when I fell off a problem and landed awkwardly. My knee is getting better now, but I’m a ways off from returning to the bouldering gym. Instead, I’m doing physio and rehab exercises, which are humbling and habit-building. This will likely continue for at least the next quarter. I’m supposed to have an MRI (not scheduled yet) which will determine the extent of the damage, and help me understand my surgical and non-surgical options. In short, I’m aiming to be back at bouldering by mid-2017; until then, I’ll be investing in rehab and preventative activities.

  5. STYLE: I really loved this focus area as well. For the first time in my life, I’ve made clothes that I love and am consistently wearing. Two of my favourite pieces include the velvet tank top, which will be part of my New Year’s Eve outfit, and oxblood pleated pants, which I haven’t blogged about but have worn the crap out of. The jersey dress, though incredibly soft, has proven impractical – a bit too hot to wear inside, lacking a bit of coverage in the leg area to wear outside, and too tight of a neckband to prevent choking. I’m already planning to mod it into something else. So, though I was shooting for 5 pieces and have only really made 3, this was a great way to rediscover my flow-inducing hobby. I look forward to incorporating a less aggressive timeline into next year – say, one garment a month.

What Worked

  1. Working quarter by quarter – this timeframe is ideal for a commitment-phobic planner-obsessive like me. It’s just long enough to cause growth-inducing discomfort in terms of stick-to-itiveness, but not so long that it’s hopeless. 100 days, give or take, will be the timeframe for which I set goals from now on. Add to that monthly reviews, weekly look-ahead planning, and nightly next-day drafts, and I’ve got a semblance of a system.

  2. Theming my days – remember how each day of the week had a particular theme (DOMOREBOOK Mondays, STYLE Thursdays, etc.)? I’d say this medium-worked. I really liked having the ability to focus (a.k.a. tunnel-vision) on a particular thing per day, but also, knowing myself, the rigour to switch that focus to a different area the following day. For the next go-around, I’ll be even more stringent on having themes for each day of the week and adhering to them. 5 categories seemed to work great – one per workday!

  3. Topic variety within a routine – my constant conundrum: without a routine, I’m lost; with a routine, I’m bored. So, having a daily structural routine mixed with a smorgasbord of exploration areas tends to go well.

  4. Concrete goals – I mean, everybody says this, but does everybody do it? The cliche goes, “if you set goals, work toward them and don’t reach them, you’ll still be further ahead than if you hadn’t set any”. My inner perfectionist is barely breathing now (after three years of beating him senseless in the startup, what do you expect?), so this banality is finally allowed to fully apply to yours truly.

  5. Working on awesome, interesting stuff – this one again could be obvious, but I fear I’d previously neglected this simple truth. If the stuff you’re working on bores you, or otherwise causes negative reactions in you, stop bloody working on it. Find the stuff that makes your little heart person pump the air with his fist. Work on that.

  6. Trying shit – how do you find the fist-pumping things? Try a bunch. I want to do even more of this in the new year.

  7. Killing shit – and, of course the corollary: kill the things that aren’t heart-person-fist-pumping. Let them the hell go.

  8. Time for reflection – this is so key for my horse-blinders-on tendencies. Because I process things through introspection versus talking through them, this means planning for, carving off and fiercely guarding complete switch-off alone time.

  9. Goal aggressiveness – I don’t think I completed a single sabbatical goal in exactly the way I’d set out to. However, this in no way diminishes my motivation (your mileage may vary); in fact, if anything, it increases it. I’m not the self-congratulatory type – in fact, I am very much the self-flagellation type; this is why setting goals that are always just out of reach works for me.

  10. Forgiving adjustments – as things worked or didn’t, I tweaked. Cue another heavy sigh from the dying perfectionist.

What Didn’t Work

  1. Injury – yes, this was an unfortunate accident. However, I think it’s time to admit something to myself: I’m pretty injury-prone. It was part of the reason I’d quit weight-lifting earlier in the year. While there isn’t much I can do to change chance, I feel that preventative measures are worth exploring.

  2. Sickness – I’m currently at the tail end of a cold. That’s twice in as many months! Hence, another area in which I’d like to research bulletproofing.

  3. Falling off the bandwagon in the middle – this is to me what inability to act is to Hamlet: a tragic character flaw. I’m a fantastic starter and finisher, but I am a terribly shit middler. I’ve attempted to remedy this previously through settings various timelines and establishing routines, which worked to a degree. Definitely requires more work!

  4. Working on “meh OK” or “weak yes” things – as Dr. Alex would say, “just stop it”. A simple prescription that I’ll just have to stick to.

And Now, to Review 2016 Resolutions

  1. Don’t let Travelabulous Inc die: it’s certainly on life support with some major changes afoot, but not dead. Check.

  2. Question everything: suuuuuuuper-check. Throughout the year, and especially through this sabbatical, I tore apart most things in my life and started from first principles: medications, workouts, business, relationships, hobbies, next steps in life. You name it, I questioned it.

  3. Make egg-white cocktails: I can’t believe it, but this is the resolution I failed to keep. This was meant to be a lay-up that I’d have completed over last winter break, but somehow a full year later I still don’t know how to magic these. Maybe I can sneak in a quick practice round tonight? In either case, I’m at peace with totally blowing this resolution.


  • Vietnam/Thailand and Paris trips

  • Cooking with Chef’s Plate

  • Discovering bouldering

  • Doing more: axe throwing, board game playing, middle-of-the-night drag-my-friends-out meteor shower watching, cocktail crawling, etc.

  • Getting actual money in the bank from equity investors

  • Giving a talk at Mindtrust

  • Getting to work with Jeff again

  • Taking a sabbatical

  • Volunteering at SaaS North

Low Points

  • Running out of cash at Travelabulous

  • Injury

  • Trying to talk through things that I needed to think through; I wasted a lot of time on this

So What’s Next?

Now that, my dears, warrants another post. Look out for it next year (har har)!