#005 — Harvest

We all, in some way or another, seek some sort of purpose in life. Some find it in the work they do, others find it in the people they surround themselves with, and still others shine the light inward and try to find meaning down in their heart of hearts.

But for me, I’ve only ever been able to find meaning in the harvest.


Another way to put this, is that I’m outcome-oriented to an extreme degree. When I see useful things come about, I rejoice no matter how great or how little effort were put into producing them… no matter who was involved in producing them… no matter whether the journey was pleasant, painful, or prosaic.

This is a blessing and a curse. On the positive side, it means I have a high degree of tolerance for the messy, difficult aspects of life–both in my own life and in what others share with me. But on the negative side, I can’t relate to people who let their own struggles (or worse, the struggles of others) become a focal point in life.

So in my view, toil is a natural state of being and the reason why we accept it is because we know that it’s the movement of our hands in the dirt which sets up the conditions for future harvests. And disappointment and failure are also natural states of being, because we can only control the effort we put in and the knowledge/skills we bring to the field, not the end results of that process.

I make it sound as if this is somehow an unemotional state of mind. It’s quite the opposite, my inner narrative is a maelstrom. But so long as some of the seeds I plant each day eventually grow into harvestable crops, my sense of purpose remains intact.

#004 — Responsive planning

Two things are true about me: I am extraordinarily undisciplined, but I manage to get a tremendous amount of productive work done.


I don’t know if I’m just wired up weirdly, or whether it’s a case of “there’s more than one way to do it”–but the idea of writing up a detailed plan and then sticking to it is the stuff of nightmares to me. I write plans constantly, but they’re more like an exercise in creative brainstorming than any sort of promised course of action.

But I said I get a lot of productive work done, right? How is that possible without sticking to well thought out plans? Well, that part I’ve figured out: if you can’t be (locally) predictable, then you need to be globally flexible.

What do I mean by flexibility? I mean keeping a schedule that by default is completely and utterly open. So when you look at a 12 week slice of my life, there may be a handful of deadlines, meetings, and other responsibilities sprinkled in, but 90% of my time is a blank canvas–which I can fill in with whatever I want.

Of course, that’s a bit misleading without some added context. My workload and my list of “things I owe other people” is massive, mostly because of commitments made years ago that haven’t fully cleared my system since I switched to this new way of working about a year ago. And so there are always dozens of different things competing for my attention, even after I weed out all the “nice to have” and “interesting but non-essential” responsibilities.

So how do I keep track of all of those things? Do I use some huge “Getting Things Done” system in which I have a comprehensive list of everything I need to do for everything and then just churn away at whatever catches my eye whenever I have time to work? No.

Instead, I use theming to guide my work. I whitelist a handful of core activities (I.e. working on my book, training my apprentice, etc.) and then give myself full permission to spend as much time as I want on those activities. I only allow myself a handful of these themes at any point in time (Ideally 2-3, no more than 5)–and these then become my primary measure of progress for as long as I chose to focus on them.

But having themes does not mean focusing with laser-like precision on these tasks and these tasks only. It only means that if I were to summarize my work over the period of a few days or a few weeks, those themes ought to be visible in my output, and stand out against the background (AKA “Everything else I do”) — 60% on theme work is just fine, 30% is a criminal lack of focus.

For the “everything else” side of the equation, I treat it like a flow. I keep a big stack of unlined index cards nearby at all time, and when an idea comes up or I’m reminded of some responsibility, I write down notes on individual cards that just pile up on my desk. I try to scope them to actionable, deliverable tasks, but sometimes they are just vague notes that are meant to serve as reminders that will later be turned into several more specific cards. Several times a day (when I’ve got a bit of downtime, or when I’m tired of working “on theme”) I shuffle through this deck, reordering it based on what essentially amounts to gut feelings combined with new information combined with a rough simulation of what my schedule might look like over the next few days.

When that pile gets huge (and sometimes it does), it’s a signal to me that I need to either set aside time to burn through some of the stuff that has been piling up, decide to declare bankruptcy on some of the tasks/projects, or most radically, switch up my themes so that whatever is generating the lionshare of all these “Everything else” cards becomes my main area of focus for a while.

This is an idealization of what I actually do. But I think it’s pretty close.

#003 — From the heart

I am tired of endless stories about empathy, and about how our work ought to be human. I am not tired of those ideas of course, just the stories around them.


Human? Great. About People? YES! Empathy? Better have it.

But you know something? Humans? They’re messy.

So stop writing clean Medium think pieces.

Stop writing ebooks.

Stop tweeting.

Just stop.





Before you tell.

Others about how wonderful…

Being a pure human, from the heart.

Can be.

#002 — Rescue

I’ve done a fair bit of rescue work in my career, where some business or team was on the verge of falling apart–and it was my job to help them glue it all back together.


Most of these rescue projects didn’t start as rescue projects, though. They started as trainings, or a bit of contracting work on some new product that the main team was “too busy” to work on. But soon enough, it became clear that would be a total waste of money; and so we’d often end up going back to the drawing board.

There are a handful smoke tests I use for detecting an unhealthy work environment:

  • Poor financial planning, i.e. chasing the current quarter’s billables rather than having a reserve of at least 6 months built up.
  • Roadmaps that are 10% complete despite being 50% of the way through the original timeline, but haven’t been modified to reflect the new reality yet.
  • A high amount of conflict with outside vendors, clients, and other third parties.
  • A high amount of internal conflict (which is harder to spot, because it doesn’t always mean aggressive behavior but can be seen through various forms of non-participation, avoidance, unfulfilled commitments, etc.)
  • Or, in company cultures that promote a “happy” workplace, a lot of encouragement that sounded mostly like consolation, transfer of responsibility, wishful thinking, and excuse-making rather than support and celebration of real progress. (These places are THE worst, by the way!)
  • A collective delusion about how things will get better “over the hump” — where the hump may be anything from a new investment round, to a new product idea, to a new business partnership, you name it.
  • An ongoing state of emergency. The ideal amount of urgent unplanned work (particularly when it’s in response to customer complaints) is 0% — anything over 20% is a warning sign, anything over 50% is a “House on Fire.”

I don’t do rescue work anymore, because it’s immensely draining and painful psychologically, and you need to get the timing exactly right otherwise no matter how hard you try things will still fall apart.

But the key thing that I always did in this sort of project was first to go around and listen to each person involved in a business (and more importantly observe their actions)–developing as much context as I possibly could around their situation.

From there, I would show (with data) exactly what the current state of things were. And then finally, I’d present a plan for the entire business that was so simple that it could fit in one person’s head. Not a perfect plan, not a permanent plan, but a working plan that could be executed on that day.

This is the hidden asset of a business in crisis: If nothing is working, then something that does work, even a little, is worth trying. So you simplify, and you simplify, and you simplify. You focus on a handful of basics: customer service, delivering valuable work, and making money. And you do this small-to-big, almost like paying down a debt snowball.

This starts to create a culture of health and safety again, and a culture of progress. You then need to convince people to pour their whole hearts into the game, and that’s a little harder, because emergency states demoralize everyone. But sometimes when people see even the faintest glimpse of a light at the end of the tunnel, they’re willing to run towards it–at least for a little while.

*  *  *

Funny enough, most of what I did in my rescue work can be learned from watching the British version of Ramsay’s Kitchen Nightmares. That sounds a little bit silly (especially if you’ve only seen bits and pieces of the U.S. version where it’s cut to show him just yelling all the time), but it’s legit.

If you watch that show, you’ll see the same pattern over and over again.

Simplify the menu radically, teach a handful of things that can be done well, improve the ROI per dish sold or if not that, the consistency and speed at which dishes are produced. Drive up the quality and consistency of customer service. Get to the root of interpersonal issues and shake them out, make it clear that without doing so, it’s the end of the line. Remind people why it is they’re doing what they doing in the first place–what the mission was. Cut out the genuinely toxic people from the equation. Bring in new people who can model good behavior, etc. etc. All of this together is just straight operations tactics, but the key is to apply it all at once with overwhelming speed and crispness of execution.

As I said, timing is critical. Most fires are already burning high by the time you pick up a hose. But sometimes, you get lucky, and you can turn a place around.

#001 New beginnings

If you’re here, then you are at the entry point of a whole new journey for me.


You may be looking for an explanation about this sudden change in approach. The short story is this: I’ve learned how to be loud, how to get attention on social media, how to dig in and reach people in various ways. But I’ve had enough of that for now.

Now I have to retrain myself how to work in a more quiet way–a way that doesn’t involve constantly looking out into the world to see what everyone else is up to, reacting to it all, chasing after it all.

Instead, I must learn to walk my own path. On my own terms.

So as of today–as of this moment–I’ll begin an exercise in daily writing, free from the hustle and bustle of social media. If you’re a close friend or colleague, you already know how to reach me. For everyone else, please be patient while I spend some time away from the bazaar, figuring out who I want to be.