The Journey Ahead (Photo of Hallgrimskirkja, Reykjavik)
As part of my quest to be more intentional with my time, I’m testing my hypothesis about work that I will love…
My hypothesis: become a world-class, startup product guy.
- World-class. Dream big.
- Startup. I’ve lived at one for the last four years and – despite the lack of balance, the ups & downs, the uncertainty – I wouldn’t have it any other way.
- Product. I’ve learned that my general interest in everything (engineering, business, people, creativity) actually works to my favor in some fields; this happens to be one of them.
Hypothesis As A Directive
I’ve been thinking of this hypothesis as my directive that can guide decisions across my professional life… (who I surround myself with, how I spend my professional development time, where I work, etc.).
Herb Kelleher, CEO of Southwest Airlines, once told someone, “I can teach you the secret to running this airline in thirty seconds. This is it: We are THE low-fare airline. Once you understand that fact, you can make any decision about this company’s future as well as I can”.
Source: Made to Stick by Chip and Dan Heath (re-inspired by Ash Maurya)
Deliberate Practice
Between now and that potential future, I expect all of the fun and discomfort that comes with deliberate practice – my favorite term that more accurately describes Gladwell’s 10,000 hour hypothesis in The Outliers.
The best people in any field are those who devote the most hours to what the researchers call “deliberate practice.” It’s activity that’s explicitly intended to improve performance, that reaches for objectives just beyond one’s level of competence, provides feedback on results and involves high levels of repetition.
For example: Simply hitting a bucket of balls is not deliberate practice, which is why most golfers don’t get better. Hitting an eight-iron 300 times with a goal of leaving the ball within 20 feet of the pin 80 percent of the time, continually observing results and making appropriate adjustments, and doing that for hours every day – that’s deliberate practice.
Source: What it takes to be great by Geoffrey Colvin
My Plan of Action
To kick off that deliberate practice (and to stress my hypothesis), I’m going to do a deep dive on what it means to be a world-class, startup product guy.
Here’s the plan I’ve devised (which was pretty heavily inspired by this post from Michael Ellsberg), which will be the anchor for my Pick Four “Work” objective over the next 12 weeks:
- Practice - continue to be a product manager at work and find ways to get involved with more/different people outside of work.
- Read – read a great “product” book every 1-2 weeks; this’ll include books on design, leadership, lean startups, etc (and not just books about “product management”).
- Interview – find the people I want to emulate (ideally world-class, startup product folks) and talk to them about their art (process, challenges, interests).
- Write – do a little critical thinking about each of the above and be write it up on this blog.
Disclosure: this little plan has been underway for a little while, but now it’s finally on “paper”… More soon. ;)
I over-commit. Constantly.
GTD has been HUGE in helping me get more done, but learning how to get the right things done – figuring out what to focus on and commit to - is a different story.
One symptom of this problem: every time I decide to add something new to the mix (from pomodoros to blog posts, morning routines to meditation), it often feels like a brand new effort separate from all the others. In order to succeed with the new habit, I typically have to sacrifice something in another area of my life… Feels wrong – if I’m focusing on the right things, I would expect more of a snowball effect where each new upgrade becomes easier because of past progress.
So in place of another productivity trick or personal development effort, I have decided to put my energy into a new system. A better machine. Something that will help me balance my broad set of interests with the focus it takes to ship the things that have a meaningful impact.
Enter: Pick Four
Name of my new system = Pick Four.
Basic premise = pick four well-balanced goals, then make daily progress towards those goals over 12 weeks.

I won’t overplay this particular choice because there are plenty of systems out there, and behavior change isn’t system-dependent (doing the work is still the hard part). I landed on Pick Four primarily because (a) it’s a workbook, and I like workbooks (b) Seth Godin is its author/curator and I like his style (c) I saw it mentioned somewhere on Julien Smith’s blog and that guy makes a lot of sense to me.
It also happens to have some of the elements that are handy for eliciting behavior change, including:
- Goal setting - the workbook starts by asking you to envision long term goals, then reduces them to short-term steps you can take to achieve those goals
- Timeline - the program only lasts 12 weeks
- Focus - you can only pick four things to direct your attention towards
- Motivation for my elephant - engages the emotional self by focusing on what you want your life to look like
- Daily and weekly review - as with GTD, the regular evaluation is key
- Written contract - clever, subtle trick; one of Cialdini’s Weapon’s of Influence
- Social contract (optional) - the workbook ships in 4-packs so you can share with friends (Tess and I are doing this together)
Good enough to get started with.
What I’m After
I’ll cut to the chase. Here’s what I’m going to focus on over the next 12 weeks:
- Be a Better Husband – at the end of the 12 week program, I’d like to sit down together and reflect on 12 weeks of solid, steady growth.
- Long term goal = build a relationship unlike any other I’ve seen.
- Do Some Professional Development – at the end of the 12 week program, I’d like to have published at least 11 more blog posts that fall out of reading great books and interviewing smart people in the Startup/Product arena.
- Long term goal = do work that I love.
- Learn How to Train a Dog – at the end of the 12 week program, I’d like to have a dog that is incredible well-trained and know how to do it again… Tess and I have already found a ridiculously good trainer.
- Long term goal = love life and exude happiness.
- Give Back – at the end of the 12 week program, I’d like to be reengaged on a consistent basis with a great group that is making positive change happen in the community.
- Long term goal = be a community leader.
With Focus Comes Clarity
A former boss, great story-teller and good friend always harped on the importance of focus; it’s only recently that I’ve begun cultivating the discipline to stay focused… and I hope this new system will be another step down that path.
With this program, in particular, I’d like to fend off the barrage of new/fun/exciting undertakings by shelving them until I can be deliberate/intentional about which will be a part of my next 12 week program.
Should be a fun little experiment. Wish me luck.