The Unexpected Benefits of ‘Foolhardy’ Challenges

I always advocate figuring out why you’re doing what you’re doing.

In the first place, it’s the first step in making sure you’re not just doing what you’re “supposed” to be doing.

In the second place, it ensures you have a clear outcome in mind so that you know what “done” looks like and you can get there in the most efficient manner.

And thirdly, knowing your why enables you to clarify your priorities, so it’s easier to see what projects should be tackled first.

This is good productivity theory, (or management theory if you’re dealing with more than one person.)

But there’s always an exception to the rule…

However, there is one important case where you don’t need to know your why.

You want to, and you reasonably expect the opportunities it opens up to be more advantageous than the opportunity cost of pursuing it.

You know what I’m talking about. Those projects that entice you away from your “real work”? They’re always on your mind, and it feels like love? You find yourself trying to rationalize why it’s a good idea for you to spend time on it (or you try to persuade yourself to get your work done first?)

It’s easy to forget this potentially serendipitous situation when you’re prioritizing your projects and goals. For one thing, it’s intangible. Intangibles are hard to measure, it’s hard to even nail them down in relation to other potential projects. Plus, you just can’t anticipate what’s going to catch your imagination.

Another problem is that they’re generally frontiers, in terms of your understanding and experience of them; there’s so little you know for sure that you can’t even say how likely the project is to succeed, and the only way to find out is to plunge boldly onwards. Considering that there are usually many more ‘sure bets’ closer to your area of expertise, this can seem like a foolhardy choice.

The third problem is that they are often all-consuming, or nearly so. Almost every responsible business own feels guilty to greater or lesser degrees when they pursue these exciting, but potentially ill-advised projects. Whether it’s because the project requires a lot of babysitting, or they enjoy the challenge of the learning curve, or the believe in their vision of the eventual outcome, most everyone enjoys these projects, and although they might not succeed, they often do, and regardless of the outcome almost universally people are glad they undertook them.

They say things like “It challenged me.” “It taught me a lot.” “I was excited to start work every day.” “I learned a lot about myself.” Frontiers are where the opportunities are.

Frontiers are where the opportunities are.

The most famous example of these “frontier” projects are things like Google’s famous 20% time, where employees have one day a week to work on projects of their own choosing (now mostly defunct, unfortunately). It’s a person slowly working at a Master’s degree at night even though she already has a good job that she likes. It’s deciding to run a marathon. Or build a Tiny House. Or have a baby. Or write a book.

Sometimes these are business related, sometimes they are not. Sometimes they have a measurable impact on the bottom line, sometimes they just affect your subjective wellbeing (aka happiness). Sometimes they open up a door to an amazingly rich vein of experiences and lessons, sometimes you just find out for sure, “Nope, not for me.”

My Official Position on Frontier Challenges

At some point in our talks, every client asks me what I think about their frontier project. Depending on their temperament, they either want tips on how to focus on their “real work” or how to justify the time they spend on the frontier project.

Although I sometime rein in the more grandiose expectations, I’m almost always in favor of them. Why?

  1. If it’s just an infatuation, those pass more quickly if you don’t fight them. I spent 2 hours researching ice wines last night after my sister gave me the most amazing bottle. Infatuation, over. I’m still going to pick them up when I see them, but I no longer want to tour every winery and compare ice wines to raisin wines to noble rot wines. Well, I kinda do, but at $50+ dollars a bottle I don’t have that much of an interest in them. Two hours gave me as much information as I needed to know where my priorities lay.
  2. Frontier projects invigorate you. The human organism thrives on a small amount of risk. We’re wired for security, but we need to keep our edge. Frontier challenges allow you to manage your risk + engagement levels.
  3. Frontier projects force you to manage your time better. Systems are great, but because you get better at them, they tend to pick up unnecessary layers of complexity over time. If you’re tightening up on your work processes in order to free up more time for your side project, that’s all to the good. You’ll also ruthlessly weed out the busywork.
  4. Frontier projects have unexpected benefits. What these benefits are is always different– that’s the exciting part. Like popping a balloon at the fair to see what surprise is inside, Frontier projects bring an unmatchable level of serendipity into your life.

Many business ‘creatives’ have to push their limits or die. But I would argue that we all have that need to a greater or lesser extent. Be out and proud about your sideline projects. They demonstrate that you are fully engaged with your life.

So now I’m dying to know, what’s your frontier project? What are you obsessing over lately?


5 thoughts on “The Unexpected Benefits of ‘Foolhardy’ Challenges”

  1. My frontier project is the simplicity event I’m putting on in the Twin Cities in the fall of 2014. It has me fired up more than any other work-related project I’ve ever thought of or been involved in. Like, “pistons revvin’, sparks flying, oh my goodness I can’t wait to work on this thing” fired up.
    I know why I want to host and coordinate this event, but I’d still do it even if I didn’t know why. The opportunity is THAT amazing. Side note: my thoughts on “why” being the center of everything have shifted over the past year. Whereas I was a disciple from the school of “Why” from 2010-2012, I’ve recently been shifting (gradually) back to what. That’s mostly due to conversations with my Toastmasters buddy Sal. He’ll explain it much better than I can soon in an upcoming episode of my podcast. It’s going to be exceptional… just like my simplicity event.

  2. Well, you called me on it! My frontier project was the tiny house. But that one was really easy to justify- Spend a bunch of money that I have saved up now, learn how to build (which I’ve always wanted to learn), and wind up with a beautiful home I can live in close to rent free? I’ll take it.
    Now, what about the less useful things- like the fact that I’ve been obsessed with the idea of learning how to kite board for at least a year. I finally took some lessons last winter, but didn’t follow it up at all this summer because it’s an expensive sport to get into (lessons + gear) and I was building a house (see above).  This sport has basically no effect on my business that I can see, and it will only cost me money and time. Still though…

  3. michaelwroberts

    I think I have frontier projects every few hours, though I’m spending the bulk of my time in working towards financial freedom (AKA “kill the credit card debt”). It’s inapplicable to my blogging and my day job in the sense that I’m not going to start writing money-saving guides or anything like that. But, the hard work now is to free up more time for the frontier projects in the future.

  4. Oh man, I love the term “frontier project” for these things that keep catching my fancy. The most recent one was web design, but I think I almost always have one going. They don’t feel like work, so it somehow feels like I shouldn’t be doing them. But you’re totally right — if it’s just a momentary infatuation, I get through it faster if I just indulge it. And if it’s a longer-lasting thing, I almost always derive great value from the experience. I’ll try to quit whining about self-discipline every time another frontier project crosses my path 🙂 (New version of …SQUIRREL! ??)

  5. I’m obsessing over beading/jewelry making lately. I thought it was an infatuation, but so far.. I’m still crushin’ pretty hard, so maybe it’s the real thing. We’ll see… it’s still too soon to say. 🙂  I love your metaphors. You have a knack for choosing visuals that make sense and stick with me.
    I love the last 2 lines in your post — “Be out and proud about your sideline projects. They demonstrate that you are fully engaged with your life.” – I think that’s a message worth spreading. Because I think a lot of people dismiss their side projects as not a priority because it’s not their bread and butter. But, I think if we do that, that’s kinda like killing a piece of our soul. I know that sounds a little dramatic, but in my experience, there’s a lot of heart in those side projects – that’s why we obsess over them sometimes or think about them when we’re doing other things that pay the bills.
    What’s cool about those side projects, too, is that when someone tells me about a side project they’re working on, I tend to learn a bit more about who they are than if they tell me other random facts about themselves.. where they’re from, how many kids they have, about their 9-5, etc. etc… because that’s something they’re doing because they want to, unrelated to their responsibilities. I think that makes for another reason to be more ‘out and proud’ about those frontier projects.

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