So a few decades ago I knew I wanted to start an agency. I had plans to make creative good for awesome clients and make Scrooge McDuck levels of cash.

Here is the thing, I was an idiot, probably still am but that’s a different article for a different day. I was an idiot because I was playing the wrong game. I had no idea what I wanted, what success really was, and what winning even was.

Life is a game, there are lots of microgames we all play along the way, and some play into other games, short games lead to long games. There is actually a solid book that takes this gamification and pairs it to bets. The book, Thinking in Bets by Annie Duke, isn’t wrong. Two really key concepts here:

  1. Life is Poker, not Chess—The decisions we make in our lives (business, saving and spending, health and lifestyle, relationships, parenting, etc) involve luck, uncertainty, risk, and occasional deception — prominent elements in poker.
  2. Everything is a bet—Jobs and relocation decisions are bets. Sales negotiations and contracts are bets. Buying a house is a bet. Ordering chicken over steak is a bet, etc. In most of our decisions, we’re not betting against another person — we’re betting against all the future versions of ourselves that we are not choosing.

So with this in mind, I thought I was playing Chess. I was trying to set up the board just right and thought I knew the outcome. But life comes at you hard and fast you get some cards that you don’t expect but have to deal with.

Fast forward a bit. It’s 2018 and one of my companies is growing like crazy. I spent a few years in an entrepreneurship growth program that really pushed its members to get to that top-line revenue of 1 million dollars. As if that is a magic number that says a solo real estate agent in California selling 2 houses a year and a popcorn gift tin company with 15 part-time employees in a seasonal business are equally hard-working to hit that number. I’m being pressed to hit $1m and to do so at all cost. This was my 4th year in that program and seeing a lot of my friends graduate up to the bigger program. I felt the pressure.

I took more and more clients at all costs. Clients that were a stretch for us to service but I thought If they can just sign the contract, and pay, we’ll sort it out later. That the red flags would go away after they pay. Spoiler, they all blew up and I had a bunch of refunds and canceled contracts. I had a few staff that probably needed more time to grow, or maybe weren’t the best fit for us, but If I could just keep dumping work on their desk we could sort it out later. To this day I don’t know when ‘later’ was.

On top of all that, I was still not making any real money. Yes, I had the biggest staff ever and more top-line revenue, but it was fragile at best. And it started to all crumble. ending the year at 6% profit was the WORST. I later even wrote off more bad debt from that year bringing that margin even lower.

It had become painfully clear I was playing the wrong game.

Fast forward a few years, Today actually. I was chatting with a friend about this story and recalling some words another friend had used just that same morning: playing the wrong game. When your goal is some pie out of the sky thing, like hitting a million dollars in revenue, do you even know what that game is? Do you know the rules? Is it even a game worth playing?

See for me, and my friend, our million-dollar goals were not really rooted in reality and the game rules were nowhere to be found. It was just a random metric that will surely impress others in our industry and maybe our parents that yes, we had made it. Fun fact, most people I knew that hit that million-dollar goal, were dead broke and very unhappy.

So how do you find the game you are playing?

For me, its about the North Star. A concept I learned many many years ago. If my goal is to drive from the Atlantic coast to the Pacific coast, I head west. This is a lot like our generic goal, vague, aimless, no actions, and belongs on a dream board somewhere with an inspirational quote and a doodle.

Now, what if I want to drive from Virgina beach to Huntington beach with 1 friend, in my car for 3 days arriving on a Wednesday evening. The instructions become crystal clear. I know when I leave, I can calculate the stops for gas and food, the stops for sleeping, etc. This is a laser-focused mission with all the right ingredients for some level of success. And back to the book of thinking in bets, this is set up to be a reasonably easy bet assuming my math is right, the weather is good, and my car is in good order.

This second scenario is a clear mission and a game that can be won or lost. The former is not a game at all really.

So what game are you playing?

You have to take in all accounts of this. You must know what you want, what you are capable of, and know what’s even realistic. I can say with 1000% clarity that I’m going to win the Tour de France in 2021. Sounds pretty clear right? Those that know me, know I bike a lot, thousands of miles per year for the last 20+ years of my life. But the reality is a pro rider has 5x the mileage a year and is about 10–15 years younger than me. The likely hood of a mid to late 30s avid cyclist making the Tour and winning is pretty astronomical. I would not bet on that one.

But I can say for business, I know that hitting a million dollars in revenue is an $84k a month income and that is X number of average projects with Y staff producing that work. I know with some certainty the level of effort it takes for the sales and leads to convert to paying contracts. I also know that we have a sweet spot of profitability. That we make more money per project at one size than the other, and you’d be surprised to know that bigger projects do not actually add up to more profit. So for me, these are the rules, and funny enough, it’s not a game I want to actually play.

See, I know the stress it takes for these metrics to add up to $84k a month, and it’s not stress that aligns with my other life goals. You see a North Star is multi facted and must align with my personal mission as well. I can not be the father, husband, friend, homeowner, and balanced self I seek if I am running 100 hours a week to hit my goals with work.

So like my dreams of winning the Tour de France, the math here just isn’t on my side and the bet isn’t great. While I can not change the rules on the Tour, I can change the rules for the game I’m playing with my businesses. In fact, I make the rules in the first place so I can adjust to define what success aligns with my North Star.

My North Star

For me, my north star is multifaceted and part of a 5, 10 and 20 year game. I require work-life balance, working with people I enjoy, helping others often, and making some money along the way. I don’t expect to become a millionaire and achieve the 8 car garage for all my toys, but I’m very okay with that if all other aspects of my North Star are achieved.

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