Tracking

Into the Wilds

Venture Capital Wilderness

The suck will happen. It will happen to you and it will happen to me. We don’t have any say in this.

But we are not powerless.

We get to choose how we react to this time in the wilderness.

The Wilderness

Being outside is awesome. I am a firm believer that time spent outside with people we love is the best way to build lasting and impactful memories. That is not the sort of wilderness I am talking about in this post. I am talking about the wilds of life. Times when things get tough. Times when you feel lost and your lack of direction starts making you question if you will ever find the trail head.

I am willing to bet you have spent at least some time in this wilderness. I know I sure have. For most, it is a question of when, not if. This time in the wilderness can be precipitated by a variety of things. Relationships. Career setbacks. Struggles with health. The hallmark of all of them is that you find yourself struggling through without a clear path forward.

I wish you nothing but the worst of luck

A couple of years ago Supreme Court Justice John Roberts gave an unconventional speech at his son’s high school graduation that picked up some attention. I recently read through it for the first time and it really struck a chord with me. I have highlighted an especially impactful section below.

Chief Justice John Roberts graduation speech

I think Justice Roberts does an excellent job capturing the idea that our reactions to life define us even more than our circumstances do. I am a big believer that people have a lot more agency in life than they often believe. The Berg family motto is “Everything in life is a choice”. When something bad happens, you can choose to let it define you. Or you can choose to view it as an opportunity for learning and growth.

Tracking

Our times in the wilderness are brutally hard when we are in the thick of it. But these times also present a potentially life-transforming opportunity. Times in the wilds are an opportunity for learning, exploration, and self-discovery. When I am unsure of my next step or direction, I often think back on the philosophy of Tracking espoused by Boyd Varty. These tough times often will have clues about what your next step should be, they just often require some tracking to find them.

Look for signals in the noise.

What aspects did you like about your old job versus dislike? What were the attributes of your recently ended relationship that were healthy? Which were toxic?

Use this time to dig in and understand the things that give you energy, joy, intellectual stimulation and purpose. Double down on those things.

I recently finished David Epstein’s latest book Range. I (along with basically every person on twitter) found it fascinating and very informative. There are a lot of excellent takeaways in this book and I highly recommend giving it a read, but the one message that came across strongest to me after putting it down was the importance of “Sampling Periods.” Sampling periods are times of exploration and discovery before someone narrows their focus and specializes. I won’t go too deep into arguing the benefits of this as David does a much better job than I ever could but, suffice to say, study after study demonstrates the benefits of having a period of exploration before specialization in sports, business, science, and life.

That’s what these tough times can be. A sampling period for self-exploration and discovery. Figure out where your talents overlap with your interest and then double down on whatever that is. Keep an open mind and focus on optimizing for learning and growth over the long-term as opposed to performance over the short-term. Use these trying times in the wilds as a sampling period to discover the best fit for your skills and personality.

I know it is difficult. I offer this advice as much to you as myself. I don’t act in this way nearly as much as I would like to. But I am working my way there.

You can too.

All you have do is to remember that whenever you find yourself in the wilds of life, you are being handed an opportunity.

An opportunity to learn and to grow and to track your way to the life you have always wanted.

All there is to it is to choose to do so.