Pete the Planner: How I’m trying to get through the ‘treadmill years’

I’m bleeding money, and I think I might bleed money for several more years.

But before you run out to buy me a sympathy card, allow me to provide some much-needed context.

I’m in an expensive season of life. And truth be told, it’s been about 10 years since I’ve had a season this expensive. Yet somehow the feeling is so familiar and can induce such stress and despair, even though I planned for it and I’m ready for it. My hope is that I can help you identify your next expensive season and make it a little bit easier.

An “expensive season” is when numerous large or unusual financial obligations chirp to be fed. Calling it a season is a bit cruel, as this period can last for years on end. There are some pretty obvious seasons that you’ve likely already weathered. The classics include establishing your adult life right after you complete schooling, welcoming a child into your home and absorbing day care expenses until the child is school-age, surviving teenagers and—finally—navigating aging parents and young adult children.

Sometimes I feel like the board game Life really missed the opportunity to stick it to us.

It’s interesting how each challenge feels mildly to severely insurmountable while you’re in the midst of it. In the last few years, I’ve held onto a belief that gets me through challenging times. I hope you find value in it, too: Yes, life gets increasingly complicated. But our ability to handle increasingly difficult situations improves, too. I know I’m going to be able to survive the financial chaos of raising teenagers, but it sure doesn’t feel like it in July 2023.

The first step in ensuring expensive seasons don’t wreck your finances is to speak their name. Acknowledge they’re on the way, and prepare yourself, even if you’re currently dealing with another expensive season.

I recently heard an interview with the “heat czar” of Phoenix. His job is to help mitigate heat-related challenges for the people in the desert. He made a fascinating point about the future. It was something to the effect of (paraphrasing), “Yes, we’re dealing with record heat right now, but we need to start planting trees to provide cooling shade for the future.” That idea deeply resonated with me. Being able to look forward, even when facing an unprecedented crisis, is essential to making the next expensive season palatable.

The second step to surviving expensive seasons is to not waste the easy times. There’s nothing better than being able to exhale during the financially simpler times of your life. You should absolutely enjoy and embrace these times when cash flows easier. However, you should also keep an eye on the next expensive season.

I don’t love the final step, but it is what it is. It’s a tough one for me, if I’m being honest: Use your savings. I shivered typing that. The whole reason you put money into a savings account is to use it when you need it, but, man, I hate using my savings.

This is both a good and bad thing. The good part is that I value the money enough to not want to waste it on something trivial. The bad part is the feeling of finality when I spend it.

I’ve always vowed to give only advice that I personally follow, so I’ll at least flag advice that is difficult for me to personally execute on. But what’s the alternative? Going into debt? Exactly. That’s why I always end up using savings, then building it back up over time.

Another way I like to think about expensive seasons is to call them “treadmill years.” Because no matter how much work you’re putting in, it doesn’t feel like you’re getting anywhere. Thinking of it this way also encourages you to get moving when the treadmill years come to a close.

One last note: My personal financial challenges are relative to my own financial reality. Just as yours are. It’s a bad idea for you and me to not take our challenges seriously because we might have it better than someone else. We can both acknowledge the struggle of others and refine our financial lives. Martyring attention to your finances out of respect for people who have it worse is silly.•

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Dunn is CEO of Your Money Line powered by Pete the Planner, an employee-benefit organization focused on solving employees’ financial challenges. Email your financial questions to askpete@petetheplanner.com.