The Alarm Went Off at 3:45. So Did My Common Sense.

The alarm went off at 3:45 AM. It was time to get back on the bike.

I hadn’t spent many hours in the hammock, and with the September night temperature dropping to around 50°F, along with the occasional train whistle sounding from across the river, it had been a cold fitful night’s sleep. Nonetheless, it was time to roll.

But why was I climbing onto a bicycle in the dark after spending the night in a hammock?

I was in the middle of a 184.5-mile bicycle ride along the Chesapeake & Ohio Canal—the C&O Canal—following the Potomac River from Cumberland, Maryland, all the way to Washington, D.C.

The canal itself has quite a story. During the 1800s and early 1900s, mule-drawn canal boats traveled this route carrying coal and other goods downstream. The canal closed in 1924, but the towpath where the mules once walked has been preserved as part of the C&O Canal National Historical Park. Today, cyclists, hikers, runners, and campers travel much of that same route, passing old locks, lockhouses, aqueducts, a tunnel, and remnants of communities that once depended on the canal.

And now, in the darkness of a mid-September morning, I was traveling that old towpath with my son-in-law, with many miles still ahead of us. Along the way, I was reminded of everything I already knew about money, goals, and follow-through. Here’s what the ride reinforced within me.

Establish the Goal – Start with a number, not a wish

For years I wanted to bike the whole C&O Canal in under 24 hours. It was my “BHAG” – a Big Hairy Audacious Goal – but a doable one! Not something that I could just hop on the bike and knock out, but an event that I just needed to do or pack it in. I had a specific target and a deadline, and I determined this was the year to make the ride.

As my teammate Mark has pointed out in his article on goals, SMART goals need to be personal and rewarding. I knew I’d regret it if I didn’t at least try and I knew there would be deep personal satisfaction in completing this challenging feat.

Money works much the same way. “I want to be in a better financial position” gives you nothing to aim at. “I want to pay off the rest of my college debt by the end of next year” does. Financial goals need the same three parts: a specific target, a deadline, and a reason that still matters when you’re tired.

Plan the route before you clip in

I read articles, studied the towpath map and used AI to do research and develop a cue sheet. I did reconnaissance rides and thought through my equipment as I developed my pack list. I broke the ride into manageable segments, each with a target time.

Big financial goals become manageable the same way – once you stop staring at the whole thing and start looking at the “next mile marker.” Your financial plan could be mapped like this:

• The total: the full amount and the accomplishment date
• The path: where to save or invest and what tax strategies to use
• The checkpoints: monthly, quarterly or annual milestones to measure your progress
• The fuel stops: automatic contributions, so progress doesn’t depend on willpower
• The bail plan: a well-funded emergency fund, so a financial “flat tire” doesn’t derail the entire journey

Planning isn’t the boring part before the real work. It’s the reason the real work is possible.

Train like the goal is already real

Hope is not a strategy—and neither is attempting a long-distance bike ride on enthusiasm alone.

Part of my planning involved scheduling training rides. Those rides prepared my body, but they also taught me about pacing, nutrition, equipment, and my own limitations. Often, the alarm would go off at 4:00 or 4:30 AM so I could start biking while it was dark so I could get used to trail riding with a bike light. Sometimes I felt like riding, other times, not so much.

What mattered wasn’t the great days – it was the boring, repeatable ones; it’s the consistency. The same is true for money. Automating a transfer on payday isn’t exciting, but it’s the financial equivalent of a repeating the training ride. Nobody applauds it, but it’s the thing that helps get you to the finish.

Keep Pedaling Through the Middle

I’ve found that the toughest part of pursuing almost any goal is the middle third. The excitement of starting has worn off and become a memory, but the finish line isn’t yet in sight. That’s when you have to call on discipline to simply keep pedaling.

For us, that middle third included about five hours of riding in the dark. There wasn’t much scenery to enjoy—just the beam of a bike light illuminating the trail in front of us, mile after mile. At that point, the goal wasn’t particularly exciting. It was simply time to keep pedaling.

Financial goals have a middle third, too. The excitement of setting the goal and creating the plan eventually fades, while the reward may still be years away. This is where consistency matters most. You keep saving, keep investing, keep making good decisions, and keep moving forward—even when it doesn’t feel like much is happening.

Sometimes progress doesn’t feel like progress when you’re in the middle of it. You just have to keep pedaling.

Adapt to the Circumstances you’re given

We hit detours – some we were warned about, and others that showed up uninvited. When a towpath resurfacing construction problem blocked our progressing, we carried our bikes down into the wooded canal bed and bushwhacked our way around the mess. My bike light died halfway through our night riding. Our dinner and breakfast stops took longer than planned.

And we still finished. If I needed a perfect ride, I would never have gotten there. The same is true with money.

Every financial goal has its own version of a “closed trail:” a surprise repair, a job change, family needs, health issues, or a month where the numbers just don’t work. You’ll overspend one month, miss a contribution, or watch a market dip at the worst possible time. The goal isn’t a spotless record. The people who reach their goals aren’t the ones who avoid detours — they’re the ones who built in slack, stayed calm, and adjusted the route without abandoning the destination. It’s a plan resilient enough to survive your imperfect execution. Perfect is a fantasy. Finished is a fact.

Don’t do it alone – Other people make the journey better

I enjoy listening to wilderness-survival podcasts partly because I want to learn as much as I can about first aid, decision-making and survival techniques. One point that comes up again and again: be very cautious about tackling big adventures solo.

Fortunately, I have a son-in-law willing to ride with me at my pace. The accountability, camaraderie and moral support was invaluable. There were stretches, especially in the late-night and early-morning hours, riding along in silence, when I was genuinely grateful to have someone beside me.

You don’t have to pursue your financial goals alone either. A spouse, family member, CPA, attorney, financial advisor, and other trusted person can play an important role, and support you along the way.

Use a guide – Experience can keep you from making unnecessary wrong turns

My son-in-law had biked the C&O canal in 28 hours some years earlier. His help planning and describing what lay ahead on towpath was a real advantage. We need somebody like that for our money lives too. Whether it’s a financial advisor, an accountability partner, or a friend who asks “so how’s the savings goal going?” – having someone in your corner is not a sign of weakness. It’s a strategy.

As financial advisors, we’re the guide for our clients. We can’t pedal the bike for them, but can help map the route, keep them on the path, anticipate trouble, measure progress, help them make adjustments when circumstances change, and remind them why they started when their own motivation runs thin.

Celebrate the win!

I stood by milepost “0” having finished the ride in 23 hours and 23 minutes. I was tired, sore and smiling like crazy. I high-fived my son-in-law and took in the moment.

Celebration matters. It marks the goal as done, reinforces the behavior that got you there, and gives you the confidence to set the next one. When you hit a financial milestone – paying off a balance or a mortgage, completing a charitable gift, or reaching financial independence – stop and acknowledge it. You earned that, one unglamorous mile at a time.

This ride was personal and rewarding. I’m grateful for being physically able to do it at this stage of life, sharing it with my son-in-law, and simply having the satisfaction of finally doing something I had thought about for years.

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