Getting Comfortable with Being Uncomfortable: Lessons from Wake-Surfing and Investing

Have you ever felt that knot of anxiety in your stomach when trying something new and challenging? That’s exactly how I felt yesterday, standing on a friend’s boat, about to try wake-surfing for the first time at 46. This experience served as a powerful reminder of the importance of getting comfortable with being uncomfortable, both in life and in financial planning

I was so excited when I got the call inviting me to come out on my friend’s new boat!  But when he told me that we were going wake-surfing, I suddenly started to feel a little bit uneasy.  Despite my athletic background, doubts crept in. On the way there, I called him to reassure both of us that I was determined to get up on that surfboard. As I watched others on the boat follow instructions and navigate potential mishaps, I realized they had all likely felt like I did at some point. They had to find a way to get comfortable while being uncomfortable.

This reminded me of my 16 years as a financial advisor. The number one concern I hear from clients is discomfort with the economy or the stock market. It doesn’t matter who is president or what party is in power; this discomfort seems pervasive. I felt like my friend driving the boat, teaching me how to wake surf. He pointed out key strategies for success and reminded me that I had a life preserver on. He assured me that, as a skilled boater, he would keep me safe despite potential risks.

There’s no guarantee of avoiding peril

Similarly, I remind my clients that the US economy has remained a world leader through many perilous times, driving innovation and growth. Our stock market has historically been a fantastic place to grow wealth over time. Staying invested for the long haul can help you take advantage of opportunities to grow your wealth and achieve long-term goals. There’s no guarantee of avoiding peril, but as a skilled advisor, I help navigate these uncomfortable feelings. Ultimately, getting comfortable with being uncomfortable makes us vulnerable. Still, even through our worst fears about the country’s direction and market volatility, we stand today with the largest economy we’ve ever had and the stock market at all-time highs.

After the financial crisis of 2008, trillions of dollars were pulled out of the stock market and never returned. Banks offered the lowest interest rates in decades, yet investors felt uncomfortable returning to the stock market after it dropped 57% during the crisis. Since the market bottomed in 2009, the S&P 500 rose from 666 on March 6, 2009, to 5,567 at the start of this year. That’s tremendous growth. As of today, it’s at 5,611. From the bottom to the beginning of this year, that’s a return of 716.16% or 14.59% per year. During that period, we endured two wars, a regional bank failure, the disastrous COVID years, and the hyperinflation of 2022. Russia invaded Ukraine, oil prices crumbled, and futures contracts went negative. Yet the market went up and down, resulting in a tremendous return over a 15-year period for those who stayed the course.

Historically, the market has been a great place to invest for the long term

Sometimes, it takes courage to get comfortable with being uncomfortable. Knowing we might regret not trying, we risk missing out on opportunities or blessings when we face uneasy situations. It doesn’t come without fear. It’s not blind trust that makes it fulfilling; it’s taking the time to think it through and decide, “I don’t want to miss out on this, so I will allow myself to get through the discomfort.”

Predicting or guaranteeing future market returns is impossible, but historically, the market has been a great place to invest for the long term to help achieve financial independence goals. Consistent saving, working with a CFP® to strategically plan for your goals, and diligently working towards those goals play a huge role in success. The market is a powerful tool. If you’re uncomfortable with the market or economy, we’d love to have a conversation. We can help balance your risk profile and exposure with your long-term goals so that you, too, can find comfort in being uncomfortable.

As I bobbed in the water and looked at my friend, I told myself it would all be good. He throttled up, and I popped right out of the water on the first try! I fell a few times and absolutely loved the experience. I’m glad I allowed myself to get comfortable with being uncomfortable—it was a day I will never forget!

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