What's Your Endgame?
Start your next career move working back from the finish
I recently caught up with a couple of friends who are contemplating career moves and asked for advice. One wants to make a move into Brand Management and wondered if an MBA is the right next step. Another is at a BigCo and feeling frustrated by the lack of ownership and collaboration. In such conversations, I tend to suggest that they think long-term and strategically—starting with their endgame.
The term “endgame” is most commonly used in movies or chess, but it’s actually a killer concept for business and career planning that I first discovered in the book A Spy’s Guide to Strategy. Author John Braddock is a former CIA case officer who worked on the front lines of counter-terrorism. His series of books combines real-life stories with straight-forward lessons.
As Braddock describes, we choose the endgame we hope to reach, then reason backwards to a series of steps and decisions that can guide us towards it. This model is useful in warfare, business, and in our own lives.
I have used my own version of the endgame model to guide my career through several key steps, and in this post I’ll share my journey in hopes that the examples provide examples that might help you plot your own path.
Fair warning: This mainly hits the summary and high points, with little mention of the pain, suffering, mistakes, fits, starts, and friendships strained and lost along the way. I’ll save those for future posts or when you and I, dear reader, can go out and have a beer again...
Endgame 1: Find My Business Path
I went to a liberal arts college out of high school with very little thought about what I wanted to be when I grew up. My strategy back then was: Get into a highly ranked school that would challenge me and open my eyes to many paths. I took a range of courses, from Shakespeare to Philosophy, started toward a Political Science major, but through summer work in office environments I fell in love with business. My college did not offer a business degree, so I went for the closest thing: Economics.
As graduation grew nearer I had no idea what kind of business or industry would be best for me. My first endgame was to find my business calling. And thinking back from there, I decided that the best strategy would be to get a first job where I could expose myself to a wide range of businesses, industries and people. I reasoned that this would naturally pull me toward where my talents and interests.
I got an offer to join a regional commercial bank as part of its management training program and it satisfied my goal. We rotated through multiple small business and corporate lending units, analyzed a wide range of industries, and I got to do everything from deep data analysis to sales and customer service.
Most importantly, I had a few specific experiences that made visceral impacts. First, I had a long-term bank client threaten to shift his account because a competing bank offered a slightly lower interest rate. It was a painful process to restructure our loan to keep it. I realized that our bank’s money was as green as the others, and we really had no competitive advantage, much less differentiation. That was not a business for me.
Second, I led the financing of an amazing entrepreneur who was making an acquisition. I sat side-by-side with he and his team through the financial analysis, business planning, and negotiation. I saw the CEO’s passion and vision. When we wrapped up the deal, I realized that I needed to escape the banking world and be an entrepreneur.
Endgame 2: Successful Entrepreneur
Looking ahead at being the leader of a business, I realized that I still had a lot to learn and needed to shift toward a general management path. I decided that going to a top, full-time MBA program would give me the formal business education I lacked and help me break into a top company where I could get further skills. My wife and I also looked at this as a life experience opportunity, so I applied to schools in large cities.
I ended up at NYU/Stern and had an amazing experience. I chose to major in Marketing because it offered a general management direction. The classes were enlightening, my classmates were a smart, diverse group from around the world, and I continued to expose myself to new directions. Specifically, I fell in love with Internet startups and did some side projects with companies like Kozmo.com.
I realized in 1997 that this Internet-thing was going to lead to huge business opportunities, and that it would the ultimate challenge. So founding a startup became the next entrepreneurial endgame for me.
Working backwards from there, I reasoned that I would need to build skills, experience, a strong network, and some career insurance since startups are high-risk. I had an opportunity to go work at Yahoo! in Silicon Valley as an early marketing employee when it was starting to take off, but I did something that seemed like the opposite: I joined Procter & Gamble in Cincinnati, Ohio.
It was a very uncool move at the time, but it was a strategic no-brainer to me:
Procter was the biggest marketer in the world with a killer training program.
I got to lead digital marketing campaigns for household name brands.
I was put on the new products team that later launched Febreze and Swiffer.
Procter gave us tremendous ownership of brand businesses, and was the career launch pad for many successful entrepreneurs.
My network swelled with smart co-workers who were going places.
Procter experience and its name on resume would be great career insurance if this dot-com thing didn’t work out.
From that decision to join Procter, I kept putting myself in positions to learn more and get closer to being ready to found a startup. I left the company when I stopped learning and joined some friends at a digital agency. That gave me the first experience in being an entrepreneur while getting closer to the startup world. After the successful sale of our agency, I spent a year at a local investment firm in order to get even closer to the startup world in hopes of finding an idea and co-founder. Sure enough, this “planned serendipity” happened and it led to starting Ahalogy. A wild startup ride ensued and ended one year ago this weekend when we got our acquisition checks and took the team to Cancun.
Endgame 3: Make a Big Positive Impact on the World
There are many books that have been written to help entrepreneurs figure out how to deal with the stress and emotions that come after you have sold your company—your baby—and realize that what you created will never be the same again. This was the end of a path that I set for myself more than 20 years ago…now what?
We sold Ahalogy in the summer of 2018 and had an earnout to take us into March 2020. So I had some time to figure out what I wanted to do with my life. That Fall I rented a lake house in Michigan by myself for a week in order to consider and plan the next business endgame that I wanted to pursue.
On the first morning I got to what I wanted to do: Make the biggest possible positive impact on humanity by leading a large, successful, world-improving business. I’ve spent +10,000 hours learning how to build businesses and I truly love the work, so how can I put this toward the most good?
Then I thought through the right steps to get to this endgame, and came up with two potential paths:
Climb the corporate ladder - Stay at the large public company that acquired us, put my skills to work in fixing issues and growing faster, get promoted a few times, then jump to a CEO spot at a meaningful, large company.
Startup up all over - Leave and create a new startup in an area where we could significantly improve the world, with people I know and trust, and apply previous lessons learned; turn it from nothing to a very big something.
So I had one endgame, but two very different paths. What’s the first step? Well that decision was pretty easy. I had over a year to go in our acquisition contract so I decided that I should take a few steps down the Corporate Ladder path and see how that looked.
And I discovered in the months ahead that I didn’t enjoy the view.
It had been a long time since I worked in a corporate environment with multiple layers of management, creeping bureaucracy, and lack of real ownership and accountability. I got to work with some great people, and our business was wildly successful, but a few months in I knew that this corporate climb was not something I could stomach, much less succeed in.
As that path looked darker, a couple of us started talking informally about Starting Up Over. We loved working together and wanted to see if we could capture lightening in a bottle again. I saw it as the clear strategic fit—we would have a much higher chance of building a world-changing business from zero than by working (and suffering) our way up through someone else’s company. And even though the odds would still be crazy long, at least we would be know for sure that we’d have fun together in the process.
Flash forward several months, and here we are at Hearty—working on a product that we hope helps millions of people discover better career directions some day.
I encourage you to reflect and set your own endgame, even if it’s many years off into the future. Be patient, open, and keep learning and adjusting course. Just make sure you’re in a position to enjoy the present as much as possible every day.