The Obstacle is the Way

The Lead - The Obstacle is the Way

We’re back! Happy New Year to you, my friends. I hope you were able to enjoy the holidays, free of illness, fires (figurative and literal), and awkward family interactions. It’s great to be here in 2026.

Your feed is being bombarded right now with resolutions and goal setting talk. Mine certainly is. I find myself skipping right on past most of it. A lot of the same old stuff you’ve heard for years. Nothing new.

I’ll take a different spin here that’s hopefully different enough that I don’t lose half of you.

One of the staples of a new year at Second Nature was the team reading a book together. It would be something that would sort of function as a theme for the year, a guiding principle.

The best book we ever went through together (in my opinion) was The Obstacle is the Way by Ryan Holiday. If you haven’t read this book, I recommend you add it to your list for Q1. It’s the perfect guide on the heels of setting your goals for the year.

The basic premise is that obstacles aren’t setbacks, they’re a path forward. When something gets in your way, what you’ll learn from that is ultimately going to make you better and create opportunities.

The key here is really your mindset and frame of reference. You lose a big deal, your strategy doesn’t seem to be working. Human nature quickly produces impatience, frustration, blame. But those things are rarely helpful, and don’t serve your ultimate end.

It starts with perception. How do you view these challenges? Do you react emotionally? Or do you take an objective view and look for the opportunity?

What follows is action. It’s pretty straight forward. Don’t get stuck in analysis mode just waiting for conditions to change. You have to “do”.

Lastly, the importance of inner resilience or “will”“. We accept the things outside our control, while remaining steadfast in our resolve.

Central to all of this is a willingness to view the things that get in your way as opportunities and continue on. I’ve experienced defeats that I had a hard time taking the emotion out of. I spent too much time wallowing with a “woe is me” attitude.

My problem with stoicism in general is that I think human emotion is a natural part of life. We feel things, there’s no way around it. We weren’t designed to be robots. But I do think this framework is helpful in general from the standpoint of problem solving.

The reality is you’re going to face challenges this year. You will experience setbacks. Your response to those things is within your control. A few practical ways to employ this.

If you’re experiencing a problem or constraint - what is it forcing you to get better at?

When something doesn’t go your way, pause. Try to think objectively. What’s within your control?

Treat friction as data, not failure. My deals are stalling, why? Am I doing a good enough job creating concrete value?

Take action, even small action. What’s the next most useful thing I can do? Don’t overthink it. Maintain momentum, even if small.

Endure. Most people quit when things get hard. Be commited to outlasting the competition.

Get comfortable being uncomfortable. Do the things you’ve been avoiding. The hard things sharpen us.

In just a few short weeks, I’ll be in a room of 70+ people at Elevate Sales Kick Off. All of us will be staring at a big 2026 goal, and wondering how we’ll get there. Everyone will have different goals, different strategies and actions they’re going to employ but there is one common denominator - we’ll each face challenges and set backs.

Those obstacles will only define us, if we allow them to. We must make the choice to view them as opportunities in service to our greater goal. I can’t make that choice for you, but I hope this helps.

Get after it.