Joyful Woman surrounded by sunflowers

The Entrepreneurial Long Game Through Joy

A recent podcast conversation between the founders of Okta, Slack, and Pigeonly, landed on the concept that entrepreneurs should focus on the “long-game”. It’s a solid listen if you’re in the entrepreneurial space. And, for the most part we agree, it is just simply that the view is a bit myopic and fails to take in the broader context that entrepreneurs are human beings above and beyond their business, whereas this advice is oriented purely around having a successful exit. Allow me to explain:

In the conversation there are multiple references to the idea that entrepreneurs should not allow themselves to be swayed by the day-in and day-out occurrences of the business. Don’t just jump at the new hot market, don’t just blindly follow the advice from the venture capitalist, so on and so forth. This is all true and sage advice.

Going Long When It Is All At Stake

But, how can we ask anyone to be so staid and strong in their approach, especially when potentially millions of dollars are at stake?  This sounds very plainly like one of those “easier said than done” sorts of things. And it is.

Until we recognize that to do any of this, to be so slow, steady, and convicted in your journey, playing the long game as they called it, requires you to be rooted in something. There must be an anchor that is keeping you grounded enough to do this. What is that anchor?

It can’t simply be the pursuit of being a successful entrepreneur. That is too vague, ambiguous, and ever-changing. In fact, it is by trying to root into such unstable ground that leads most entrepreneurs to make the very mistakes these founders are cautioning against. Instead, it has to be something more meaningfully, more personal, more consistent.

It is for these reasons we orient so many entrepreneurs on joy. Through joy they can uncover their Whole Self and build the business as an expression of who they are and as a model of operation that continually reinforces their, and their team’s, joy. Moreover, and more importantly within the context of the “long game”, joy ensures that regardless of what happens with the business something productive is always happening for the entrepreneur while, at the same time, maximizing the likelihood of success.

Joy, just like anything else,
is practiced and honed throughout a lifetime.

The Long Game In Practice

Imagine you’re a 25-year-old entrepreneur (I deal with this age group a great deal) and you’ve just started your great idea for a business. And, let’s just say, you’ve hit the jackpot, and in ten years you sell the business for a ton of money and are a newly minted billionaire. Congratulations! But, now what? You’re 35, with roughly 50 years of life still ahead of you, a giant pile of money, and…. What? What are you really going to do? How will you have meaning? How will you have joy? What was all of that even for?

These are questions that most people don’t stop to ask until they get there, if, of course, they ever do get there. Plenty, even when there, just reorient on turning their one billion dollars into ten billion. But to what end? Where are we going with all this?!

When we bring our joy to everything we do,
the outputs take care of themselves.

The Real Long Game: Life

And, this is the trouble that arises when we fail to have that root to keep us grounded in what we are truly trying to accomplish. When we have that, and, of course, we would endorse doing so through the lens of joy, the business has meaning. If it is successful financially or not becomes less important. Take the same scenario as above, but now after ten years you file bankruptcy. The point still stands.

Further, what, in a broad sense, would maximize the likelihood of the billion-dollar outcome? That you fix everything wrong with you and your business until it has no problems or that you orient the business around what has already worked so well for you in life, the contexts that have manifested joy in your life, and then allow for the outcomes to naturally play out as they will? How can you hope for anything better to emerge from the business than you operating at your very best?  So, if we can find a way for you to do that, then all the other details start to fall away.

The real long game isn't this year, this decade, or even this business. It is life. Work to win that! Win that through joy!

And, it is this point that, regrettably, the entrepreneurs on the podcast fail to capture. I suspect that it is largely due to the fact that they are still in their businesses, however successful those business may be. It is too easy to be caught up in looking at life as starting and ending with the business you are driving in the current moment, but clearly there is so much more to life than that, so many more measures of success than what happens with this business, in the short term or the long term.

So, yes, entrepreneurs play the long game, but play the REAL long game. Understand that this business is, at the very most, a big chapter in your life, but not your life entirely. Know that you, regardless of the business, are still responsible for being the best version of you, as an entrepreneur, as a human being outside of work, as someone who, at one point or another, will have moved beyond this business. And, if you can acknowledge all of that, then you can healthily begin the journey into exploring what it would mean to bring your joy, to bring your whole self, to the business you are running and leverage it as a tool to further deepen your practice of joy and not simply a mechanism for you to pursue a pot of gold at the end of a rainbow. And that, is the real long game.