Last night I took my boss out for a drink. Well strictly speaking it wasn’t “a drink”, and it wasn’t my boss so much as the boss of the whole company. Yes, perhaps out of frustration, perhaps as a hail Mary or perhaps just as a calling of a bluff I had reached out to our CEO two weeks ago and asked for some face time with him next time he was in town.

I’ve made no real secret that at the start of the summer I felt incredibly lost, without a purpose. I’ve always had a purpose and to reach a point in my life where I didn’t have the next thing lined up was… destabilizing.

But I did the hard work. I journaled. I contemplated. I reminded myself of Stoic philosophy. I considered what life would look like, and what narrative I would tell myself if I were happy with this situation. I became okay, but not satisfied.

I took my concerns to my line manager and a regular 1-1 expanded into an hour and a half of… well, if I’m honest, mostly me venting. I left the conversation unsatisfied. With nothing to show for it, nothing actionable, only the knowledge that I had gotten something off of my chest. But I don’t think it really helped myself or my boss.

The only thing that my line manager offered was the suggestion that perhaps I should speak with the CEO. At the time, I couldn’t quite work out if it was become he didn’t have the life experience to give me a good answer, whether he thought the CEO would give me better advice, or whether it was a chess move to try to encourage me to develop a relationship with the CEO.

The CEO and I left the office and engaged in a little day-to-day small talk as we walked and as we crossed the park to my choice of watering hole. We took a table out back in the beer garden, and with that we commenced.

Admittedly, I jumped right in. I took my usual brash approach of uncomfortable honest upfront. In an odd way, I know it’s a bit of a defensive mechanism. I throw everything out there with a sort of “well there you are, now you know, that’s everything”. My flooding the zone with vulnerability, actually protects me as it is difficult for a hostile other party to pick up a single thing to retort against.

However, in this instance, he listened. Really listened. And the more he listened, the more I told him. I told him things I have never said out loud before. I told him I wanted by boss’ job. I told him my current projects feel like a slow death. I told him the only time I felt alive recently was in the room with the supermarket execs closing millions of dollars of business. I told him that when I look at the guys ahead of me in tenure and seniority that I am uninspired. I told him that I’m terrified that when I look at my job in three years from now, I don’t see it being any different.

And through it all, he listened. Occasionally asked a clarifying question, occasionally asking me to dig deeper on a subject. But with it out of my system, he took only a moment to consider, and then he spoke.

He told me that through his experience of coming up in a big tech company, changing departments constantly until he became an executive VP, before starting his own companies and getting acquired time and time again. He told me, that through it all, when it comes to business, he really only sees two types of people.

There are farmers. They sweat the small things, they take their time to water and nourish the crops. They tend the fields. Farmers build cities. Farmers make civilization.

But the counterpoint to the farmer, is the hunter. Hunters move fast. Hunters change the game. Hunters sometimes create casualties. He told me that I am a hunter.

He told me that the thrill I have running towards a project on fire is no different than a salesperson closing a high-value sale.

The problem with hunters is that it is high risk. Especially early in your career, without much experience, the chance of a hunter missing the target is especially high and can be damaging.

Our executive chairwomen, I have always described in big cat like terms. Like a tiger in the jungle. I don’t understand the world in which she moves, but I recognize the talent, tenacity and brilliance of an expert hunter. Apex predators don’t worry about the prey.

As this conversation developed, I thought on this more. A leopard doesn’t change his spots. A tiger in a cage is still a killer. You might take aware the claws and the teeth, but you cannot change the nature.

The CEO went on, that at this stage it really becomes down to me finding the questions that really motivate me and then optimizing for that. He said that as a younger man, he really wanted to travel, so he took a position that ensured that he would be integration solutions for clients around the world. But as time went by, he realized that what he actually really cared about was time. Specifically, controlling his own time. He wanted the ability to control what days he worked, whether he could decide to just take an afternoon off. For him optimizing for time, drove him to high levels of success such that he could later take as much time off as he wanted. He said, that after his businesses got acquired and once before he left big corporate, he just took 4 months off. Why four months? Because three didn’t seem enough, but six was probably going to be considered mental illness by his peers.

He came up as a highly technical guy. Programmer, tech lead, the whole shebang. Had he stayed in that lane, he probably could’ve gone further fast and got a VP in big corporate, but once he got to director he moved sideways into product, then marketing, then sales. At the time, from the outside he probably looked crazy, as his peers kept going up, he zigged and zagged. He chased the next thing that was exciting. When he went into a meeting and didn’t know what they were talking about, he made sure to find out. But all of that experience, is exactly what makes him now such an effective CEO. Today, companies need technical leaders. Marketing and PR can be learnt, but the technical specifics cannot be.

But he said, knowing what you want is only half of the dilemma. The other half of the equation is realizing what you are willing to risk to get it.

Taking a well paid job, in a nice company, is obviously the safest option. But the safe option is never going to have the thrill. But the thrill comes from risks, trying new things, going to new places. Maybe that means giving up the nice job at the nice company for a jump into the unknown. Maybe it works. Maybe it doesn’t. But you won’t know until you try.

However, he conceded that there are always other factors in life, external factors outside of this immediate decision that can complicate the matter or delay the plan. Maybe that comes in the form of kids, or partners, sick parents or anything else. Sometimes life throws something at you such that the safe thing, is “the” thing… at least for now.

And that got me thinking. I’m not so concerned about the kids. The kids will be fine no matter what, I will always make sure of that, there’s never going to be a time when there isn’t food in the fridge. But I feel like I’m currently playing the supporting role in the relationship. Maybe this is her time to be experimenting with high risk situations until the papers, grants and funding role in and allow for tenure.

Perhaps, as a good husband, as a good partner, maybe now is not the time to be doing anything too dramatic.

As we drew to a close on this part of the conversation, he told me that I need to get another job. Which was pretty brutal to hear. But strap in. I came here for honesty. I came here for the uncomfortable truths that I hadn’t been able to find anywhere else. This is what I signed up for. Let’s push the ego aside and dive into this.

He said that he recognizes me as a hunter. He told me that even if my boss’ job came available tomorrow, he wouldn’t give it to me. My boss is a farmer. He loves what he does, he sweats the details, always anxious, protecting his people. To be a VP in a small firm, that is what is required and that is not me. My boss is the sort of man that will spend two years on learning 80% of a field and becoming a master, and then spending the rest of the decade mastering and polishing to get to 85%. He told me, I’m the sort of move fast and move on personality, and that as soon as I’ve got close to 80% I’ve already jumped to the next stream and by the end of the same decade I might have done three or four different things.

He told me that when we first met at some company social event, he instantly recognized that I would not work there for long. For where I was in life, our purposes were temporarily aligned but my personality was going to tire of the company.

He went on to say that in his experience across a half dozen companies or so, there’s a three year periodicity to a business. In the early days, everything is about growth and survival. Dream big. Aim big. Be audacious. These are the days when Hunters are king.

However, the business where it is now. The business has grown, the connections connected, sales made. I see it myself, every client now is no longer a 16-week proof-of-concept but a tickbox on a five year roadmap. These times belong to the farmers. Slow everything down. Add processes. Stabilize.

However, at a certain point, things become too slow and growth is required again and then the Hunters are brought back.

In his experience, each Hunter or Farmer led period is typically around three years and we’re really only just getting to the end of the first year of the farmer. That does not mean that it is wasted time. It is all preparatory work to make sure that we are ready to go when the situation flips.

He shared that timing is important. Trying to be a Hunter at the wrong time only hurts. Going to market early with a product that the market isn’t ready for just leads to hurt. You are far better off being ready for the market to start to turn and be ready with everything to ride the new wave like a rocket ship.

Wise words.

But if all of our clients are only a year or two into a five year roadmap, then no one is going to be thinking about expansion, only execution for the next few years. And if that’s true, do I really want to be a part of it?

He said there’s no shame in that. If I decide that I cannot or do not want to be part of that, he will help me find something else. When I asked, how could he possibly be okay with that, he told me, that he would want us to part on good terms, and then no matter where I go, I will remember my time there fondly and become their greatest ambassador.

That right there, is the non-zero thinking of a man of age and wisdom.

In the meantime, we discussed maybe I should take over a few internal projects that he’s wanted to get off the ground for a while. He’s just never previously had someone that isn’t afraid to get shit done. And if that takes me across departments and exposes me to new elements of the business, then I am all in.

It’s funny though. Not only did my CEO tell me that I need a new job, he told me that I need new friends and new mentors. He could tell that I am not being challenged enough. We had an entire tangent in the conversation when he used the expression “it is what is is”. This had previously been one of my pet peeves. Archetypal and exemplary in all the ways that Canada is nice but fails to be extraordinary.

It is what it is, I’ve always understood it be an acceptance of the ordinary. An acceptance of not even trying to make things better.

But he caught me. He told me that was not his reading of that expression, and certainly not the way that he had intended it to be taken.

His understanding was that things are that way now, but one must choose your fight, you cannot boil the ocean, you must prepare, wait and ready. Then when the time comes you will be ready for the adventure and make the real impact.

With hindsight, I feel like that was a little heavy handed, almost to the point of gaslighting.

But his point was this. I am still young, and it is a sign of youth that I jumped upon a thing and interpreted it entirely using my previous judgements. I did not stop to consider what he actually meant by it. Let alone stop to think his perspective. I just launched into a pre-prepared rant that I thought would make me sound intellectual.


If I am to embrace the Hunter mindset and be successful in doing so. That is exactly the sort of trap I do not want to fall into. Perhaps he is right. Perhaps I do need new friends that will be unafraid to challenge my thinking.

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What distinguishes you from other developers?

I've built data pipelines across 3 continents at petabyte scales, for over 15 years. But the data doesn't matter if we don't solve the human problems first - an AI solution that nobody uses is worthless.

Are the robots going to kill us all?

Not any time soon. At least not in the way that you've got imagined thanks to the Terminator movies. Sure somebody with a DARPA grant is always going to strap a knife/gun/flamethrower on the side of a robot - but just like in Dr.Who - right now, that robot will struggle to even get out of the room, let alone up some stairs.

But AI is going to steal my job, right?

A year ago, the whole world was convinced that AI was going to steal their job. Now, the reality is that most people are thinking 'I wish this POC at work would go a bit faster to scan these PDFs'.

When am I going to get my self-driving car?

Humans are complicated. If we invented driving today - there's NO WAY IN HELL we'd let humans do it. They get distracted. They text their friends. They drink. They make mistakes. But the reality is, all of our streets, cities (and even legal systems) have been built around these limitations. It would be surprisingly easy to build self-driving cars if there were no humans on the road. But today no one wants to take liability. If a self-driving company kills someone, who's responsible? The manufacturer? The insurance company? The software developer?