The steeper the slope, bigger the smile

Last year, Kiki and I stood at the top of Tower Three 

(a Double Black Diamond run at Jackson Hole).

The run looked terrifying — steep drops, trees, rocks, no easy way down.

We could've taken the groomed trail. The safe route.

Instead, we pointed our skis downhill and went.

That's how I've come to see most of life's big choices.

Ten years ago, I sat down one night and drew something (A Decision Tree) that quietly shifted everything.

Just two possible trajectories on a piece of paper. 

1. One line was smooth and steady. Predictable. Safe. 

Slightly up and to the right.

2. The other looked like a roller coaster — sharp drops, steep climbs, terrifying dips. But over time… it rose much higher. It was steeper but up and to the right. 

That second line scared me.

But it also called to me.

At the time, I felt stuck. I had money in the bank, a family, a career.

But I was paralyzed — not by circumstances, but by direction.

I feared people would talk about me. Judge me if I took a risk, like writing and posting on LinkedIn, or took an even bigger move, starting from zero.

But I also learned something: most of us are so busy fighting our own battles, we don't have time to think about someone else's stumble.

Companies understand this. If they want higher returns, they invest. They deploy cash. Sometimes they even borrow. That increases risk — but also increases the potential for expansion.

You cannot get outsized growth from a risk-free strategy.

Neither can a life.

At first I thought my obligation was to my husband. Or to my kids. 

Or to being "responsible."

But deeper down, it was an obligation to myself.

If I wanted the higher line — the one with bigger impact, bigger fulfillment — I had to accept the volatility.

So I started taking swings.

I left a paycheck and started down a new path 10 years ago.

I wrote a book 5 years ago— even if only a handful of close friends read it ;-)

Not because it was guaranteed to work.

But experimentation is the path to discovery.

Now 2026 is another big turn... 

Giving back what I have learned over the years to help you become more financially successful ;-) 

So you can smile like me and Caroline did when we took a risk, and reached the bottom of Tower Three!!! 

What version of you is waiting on the other side of a risk you haven't taken yet?

Tiffany Kent

Your Friendly Wealth Engagement Guide

Disclosures: Past performance is not indicative of future results. This material is not financial advice or an offer to sell any product. The information contained herein should not be considered a recommendation to purchase or sell any particular security. Forward-looking statements cannot be guaranteed.

This commentary offers generalized research, not personalized investment advice. It is for informational purposes only and does not constitute a complete description of our investment services or performance. Nothing in this commentary should be interpreted to state or imply that past results are an indication of future investment returns. All investments involve risk and, unless otherwise stated, are not guaranteed. Be sure to consult with an investment & tax professional before implementing any investment strategy. Investing involves risk. Principal loss is possible.