Planning for the Pivot

I wish I could tell you I’m the kind of guy that has the utmost confidence in the future. I genuinely admire people that will look you in the eye and guarantee you can have anything you want in life, if you’re just willing to work for it. If you eat your vegetables, do your research, work hard and practice everyday, you will always reach your goals.

I’m not that guy. I call bullshit.

Before you write me off as Eeyore, hear me out. It’s not that I’m disillusioned, it’s that I’m 35. I’ve been alive long enough to see the best laid plans fall flat. I’ve seen my best intentions and efforts squashed by random circumstance more times than I care to count. I’ve seen brilliant people fail repeatedly, despite their most sincere and honest efforts.

It seems the only thing in life that’s certain is uncertainty. The only constant we’ll ever know is change.

And really, that’s a good thing.

It’s that lack of certainty that makes life exciting. If we were always sure, there would be no such thing as risk. You remember asking that cute boy/girl out when you were a teenager? If you absolutely knew what was going to happen, you wouldn’t reminisce so fondly on the event. The butterflies on your wedding day wouldn’t have fluttered in your stomach. You could have stayed home for the birth of your first-born child. Life would be flat-line-boring. It’s completely fair to say that in a world of certainty, life wouldn’t be worth living at all.

Wanting certainty is different, and absolutely natural. Without the ability to plan, humans wouldn’t be at the top of the food chain. We use our intellect to conquer the natural world, to create the framework of our economy and society. We use it to thrive. Because of our desire for certainty, and our relative abilities at planning, we tend to look at our failures as failures in planning. We pick apart how we approached the problem and pinpoint the issue: “if I had only thought of X, things would have been fine”.

I’m here to tell you that there’s always an X. There will always be something you didn’t expect that throws you for a loop.

Why not plan for that? Why not plan for the pivot?

Personally and professionally, I’m an advocate of hedging your bets. I’m not a natural risk-taker. I don’t like flying through life by the seat of my pants, and I’m not comfortable with taking life moment-by-moment. I couldn’t turn off my analytical brain and ‘just go with the flow’ if I tried.

On the other hand, I recognize the excitement and value of risk. I understand that the willingness to take risk is why some people are wildly successful and happy, and others are just stuck in the rut of life. When I die, I want to know that I took the big risks that scare people. I want to know I took the chances that others didn’t. Whether I win or not, I want to know I tried.

I realized years ago that these 2 philosophies are not mutually exclusive. If you line the ground with pillows, you might not fly when you jump, but at least you won’t die when you hit the ground.

For example, I got my MBA because it makes me more marketable as an employee if my business fails. My wife and I have paid off all our debt and live well beneath our means so that I have more personal runway to start a business. Is that as exciting as some of the stories you read about? Probably not. But it makes a hell of a lot more sense.

To the devil’s advocates and consumers of entrepreneurship-themed media out there, you’ve undoubtedly heard “If you have a plan B, you’ve already failed”.

Obviously, I don’t buy that line of thinking. For one, it assumes that you can predict the future with your Plan A — that if you just try hard enough, you’ll succeed. Again, this assumes you can literally predict the future. Secondly, it minimizes the fact that catastrophic failures can be fatal for the risk-taker. There’s countless entrepreneurs that end up bankrupt because they ran up enormous amounts of debt financing a business that failed, then take a “safe job”, scared away from entrepreneurship forever. Some run themselves to such a dismal situation they kill themselves.

The equivalent of this, in a non-business context, is risking death for some adventure because it would somehow make you more likely to succeed. It’s like not wearing your motorcycle helmet when you decide to see how fast it goes, because you can see the tiniest bit better without the helmet. Anyone without a death wish would tell you that’s ridiculous.

My point is that you should always position yourself for the pivot — personally and professionally. Here’s how:

  1. Minimize debt:

Without getting into a finance lesson on the “benefits” of debt (I’m well aware, fellow MBAs), debt equates to risk. When you remove that risk, you’re free to take risks in other avenues. Whether you’re a person taking a job you’re excited but unsure of, or an entrepreneur launching a product in an unproven market, avoiding debt gives you more freedom of choice, increases your willingness to take a risk, and greatly reduces the consequences of failure.

2. Consider failure in your plans: ask “What If?”

The all-or-nothing mentality is not completely merit-less. When your options are success or death, you’re probably a little more likely to succeed, sure. But considering the ever-present X factor, asking, planning for that ’what if’ makes far more sense than the alternative. The next time you’re planning a big venture, don’t forget to think about failure, and don’t be afraid to spend some of your time and resources to address those risks.

3. Consider your efforts as the measure of success, not the results of your efforts.

This one’s tough. But when your self-worth comes from outside of yourself, you’ll always be inadequate.

There’s a strong criticism of the ‘everybody gets a trophy’ mentality, and believe it or not, I agree with the criticism. If you don’t win, you don’t get the spoils of victory — by definition, you don’t deserve them. But there’s a difference between having a victory parade thrown in your honor and being satisfied with your life. In reality, most people don’t even play the game. If you have the courage to act in the face of potential failure, to play the game and, maybe, get your nose bloodied, you’ll find yourself much happier in the long run. And if you do so often enough, the odds are really good you’ll end up hitting at least a couple of home runs in the process.

There are those that will continue to believe that having a backup plan is an excuse for failure, and I’m ok with that. Certain people will look life in the eye and claim that manufactured certainty is the only formula for success. Planning for the pivot isn’t for everyone. But the fact that businesses are embracing “agile” culture, and debt avoidance is becoming a more popular principle in personal finance are strong evidence that I’m on to something.

It may not be as sexy, but preparing for failure is the only way to succeed. Play the game, but plan for the pivot. In life, failure’s not an if, it’s a when.