How to Win Multiple Games on Different Time Horizons (and Why 5-Year Goals Are Bullshit)

Life is filled with games: every person you meet is playing a slew of different games simultaneously, often with dramatically different end goals than the games you yourself might be playing. The key to navigating this confusing life-sized playing board and not getting suckered into playing someone else's game is to accurately identify what games you want to play and then playing them to the exclusion of all others.

However, we don't play just one single game at a time. Instead, we're always playing multiple games toward different ends. At its most basic level, this multi-tasking is required in order to live a normal life, and frankly—survive. You need to win the games of physical health and fitness, happy and healthy relationships, mental and emotional stability, and have a strong career plan—at a bare minimum.

I like to categorize the games I'm playing based on the amount of time that it will take for the game to be won or the outcome to be achieved. The three timelines are: the short game, the medium game, and the long game.

Playing Multiple Games to Achieve the Same Goal

Once we realize that we're always playing many games simultaneously, we can use that knowledge to hack the system and increase the odds of accomplishing our goals and winning our games. Instead of staking all of my hopes on just one method of actualizing my goal or living out my values, I try to create distinct games across all three time horizons that all lead to the same ultimate end goal.

I use this strategy with my professional career, with my personal relationships, and most importantly here, with my value of living a life that's closely connected to nature.

The Short Game

The title of this blog, "Outside 365," is the summation of my short game to live a life that's in line with my values of connection to nature and outdoor adventure. Since it's a short-term game, I play this game every single day: I go outside and move my body at least one mile Every. Single. Day. This was the core idea that launched this blog and launched a total transformation into this lifestyle.

The short game can be incredibly powerful. Committing to taking one action every single day to live a life that's consistent with your most important values is a powerful way to live. If you live this way, you know that even if it feels like everything else in your life is going to shit, you've done one thing today to create the life that you truly want to live.

I've been writing about this short game here on the blog for several years now. So, I'll turn my attention to the medium game.

The Medium Game

While the short game is very engaging and requires a time investment every single day, the medium game is perhaps the most interesting one. The medium game usually consists of a bigger goal that will move you towards the ultimate goal, but it will take a fair bit of time to come to fruition. While it won't happen overnight, I try not to plan any medium games that will take more than six months to complete, or a maximum of one year.

Working toward moving into a van full-time is one example of a medium-term game that I played. It took about nine months of consistent work to actualize this goal—and we didn't know that it would take so long when we began the process! During that time, I had to work diligently in partnership with Christine on many different fronts towards the goal of purchasing the van and moving into it full-time.

We had to do the research to determine what van to purchase, whether or not we could do the work ourselves, and what builder to work with. We had to figure out how to budget and save for an expensive van purchase and deal with roadblocks to closing the deal. We had to navigate supply chain disruptions due to COVID, schedule delays, and so much more. We overcame a whole host of unexpected obstacles that cropped up during this process.

The point is, this goal took a lot of work over many months in order to achieve it. It didn't take a decade, but it couldn't be done overnight, either. But most importantly, the van wasn't the ultimate goal. The ultimate goal was the lifestyle and the adventure that the van enabled. Working and achieving the goal of #vanlife was important because it better enabled outdoor adventure.

The Long Game

Long games are generally games that will take at least 10 years to complete, if not more. For me, most of the potential long games fall into the bucket of liberating yourself from the bondage of employment, e.g. retiring. And at the risk of stating the obvious, the point of striving to liberate myself from the bondage of employment is to enable longer and more epic outdoor adventures.

Humans have a hard time delaying gratification, so trying to make a plan and play a game on a decades-long time horizon might be the most difficult of all games to play. This is precisely why many millions of Americans are woefully unprepared for retirement, even by the time they reach their 60s and 70s. (Source) They haven't successfully played their long game.

The key to winning at the long game is to not sacrifice one game in order to win a different game. Yes, we can only live in the present moment, but we can't be so focused on short games that we neglect the strategies that will allow us to win the long game. Every dollar that we spend in the short term is a dollar that isn't invested in the long-term game of investing for retirement. Similarly, every dollar that we save for the long game is a dollar that we can't spend to actualize medium-game goals, like traveling internationally or buying a van.

The secret sauce consists of figuring out how to balance all three of these games on their different time horizons so that you can ideally win at all of them.

Shorten Your Time Horizons

The second critical strategy for winning at these various games is to shorten your time horizons. One of the questions that's popped up in Tim Ferriss's work and originally comes from Peter Thiel is, “If you have a 10-year plan of how to get [somewhere], you should ask: Why can’t you do this in 6 months?”

While it's rarely possible to move a long game into a medium game, and only slightly more possible to move a medium game into a short game, it's still a question that's well worth considering. Simply asking this question of yourself forces you to challenge your preconceived notions and identify hidden barriers that are blocking you from winning your games.

For example, I once had a long-term goal of eventually traveling the world full-time. I thought it would take at least 5-10 years to achieve this goal, putting it in my long-game bucket. But after reading this question and asking myself how I could possibly make it happen sooner, I realized that many of the challenges that I thought prevented me from traveling full-time were just simply not true. Instead, I was able to make a plan to start traveling domestically within a week and internationally in less than six months. These moves kicked off four years of full-time travel—longer than I ever thought would be possible!

I effectively moved a 10-year long game into a medium game that became a short game before I knew it.

5-Year Plans Are Bullshit

If you've been paying attention, you'll have noticed that there's a pretty substantial gap between my one-year maximum time horizon for medium games and the 10+ year time horizon for long games. This isn't an accident.

It's because 5-year plans are bullshit.

"Where do you see yourself in 5 years?" is such a stereotypical interview question that it's become a cliche. I'm so glad I've never been asked this in an interview myself because I'd have to tell the interviewer to their face that 5-year goals are bullshit—and here's why.

10-year goals are dramatically easier to make than 5-year goals because you have so much time to actualize and make them happen. You can spend years setting yourself up for success. The magic of compounding interest has time to work for you. You have enough time to invest your labor and energy into turning your goal into a reality. You know that you probably have enough time to make it happen.

On a 6-12 month time horizon, you have a rough idea of what you might be able to accomplish. The next year is close enough that you can almost taste it. For example, if you're planning a big trip, you'll need to actually click the button and buy the plane tickets soon.

Beyond 12 months, the future is remarkably hazy. None of us has a goddamned clue what the future holds, and claiming that we do is abso-fucking-lutely delusional. For example, I'm currently re-reading some of my old journals, and in them, I'm hashing out international travel plans for the next 12-24 months. The date on the entries? January 2020. No amount of planning could have prepared me for the black swan event of a global pandemic that completely halted international travel.

Thankfully, if we apply Peter Thiel's question to games that we originally thought would take 2-5 years, we realize that they can almost always be completed in dramatically less time. While moving a 10-year goal down to a 6-month goal can often be impossible, moving a 3-year goal to a 1-year goal is often much more achievable.

It is possible that the spreadsheet might tell you that certain financial goals will take, say, five years to come to fruition. But many times this is the case, I'd argue that the 5-year time horizon you're looking at might be a 10-year goal that's halfway completed.

Parting Thoughts

I realize that this type of thinking may be new for some people who are reading this. If it is, don't rush through it—take some time to consider. Take some time to write down the games that you're already playing and the games that you'd like to play. Then, bucket them into these three different time horizons, and think about how you'd play each game differently depending on the time horizon.

Finally, for the ultimate power move, ask yourself what it would take to move a long game to a medium game, or move a medium game to a short game—and then DO IT.