What to Do When the Finish Line Seems So… Far… Away

What to Do When the Finish Line Seems So Far Away

This is a guest post by Jason Hull.

“Anyone can run a hundred meters, it’s the next forty-two thousand and two hundred that count.”


I am the first to confess that I didn’t exactly have my financial life together in my 20s. I lived beyond my means when I was in the Army and then started graduate school while still mired in a pile of credit card debt.

I wasn’t exactly the poster child of fiscal responsibility at that point.

Fortunately, by then, I was on the brink of being engaged, and my eventual wife was one of the noteworthy ones who had her financial act in order.

I wanted to be like her.

However, she had to change jobs to move to Virginia to be with me, and between a new job for her, me being a full-time student who picked up a little money teaching at Kaplan, and the cost of living in Charlottesville – one of the most expensive areas to live in Virginia – we were barely making ends meet and paying minimum payments on my old credit card debt.

I remember feeling the shame of having to admit to her my past financial transgressions and see the Visa profit statement that came every month in the mail to remind me of it. I felt badly that she’d, in my mind, have to carry me along until I graduated.

So, even though I knew we were going to eventually pay off the credit card debt, that day seemed like an eternity away.

Once I landed a law firm internship, I was able to roughly calculate how much I’d make per month and map out exactly how long until we could tell MBNA to kiss it.

It’s what kept me motivated.

I faced a similar situation a few years later, although this time it was with our mortgage. We spent several years occasionally paying extra on the principal, but never really attacking it like it was a burden on our very souls. In about 2008, we got religion, so to speak, and started going after the mortgage with as much extra money as we could throw at the problem.

The problem with a mortgage is that it doesn’t go away quickly. It took three years of discipline, aggression, and manufactured luck to kill it off.

We live in a society where we seek instant gratification. We have 453 channels on our cable TV, so if we don’t like what’s on the tube, we can immediately flip to another one, and keep flipping until we find the Jersey Shore rerun that shows the most footage of The Situation’s six-pack.

Paying off debt rarely has an instant gratification moment. It can feel like a long, long, long slog.

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How do you keep motivated when the finish line seems so… far… away?

When it comes to money, I’m a planner. Not just professionally, but behaviorally. I have models that tell me how much we could withdraw monthly if we quit our jobs now, when we could afford to buy a rental property, and how close we are to our budget each month. I may be pretty catch-as-catch-can in other aspects of my life, but my goodness, I almost obsess over what it will take to get me to my financial goals.

After deciding that I was first going to get rid of my credit card debt, and then later, to get rid of the mortgage, it seemed daunting. I knew I needed a plan.

So here’s what I did:

  • Figured out my “graduation date.” I knew that if I paid a certain amount each month and then paid extra when I received bonuses or other income, I could be rid of the anchor by a given time. Having that date provided me with some certainty, knowing that, at worst, I’d be rid of the debt by my “graduation date.” If you’re using ReadyForZero, then you already know this date.
  • Set interim celebratory milestones. The ideal way to pay off your debt is to significantly ramp up your income so that you have more money to throw at the debt. However, most people won’t wind up with game-changing increases in their income, so they’ll have to suck it up and ramp down the lifestyle. It was, after all, the lifestyle that got most of us (not all of us, but most of us if we’re honest with ourselves, including me) into the debt-burdened position in the first place. However, all work and no play will kill motivation. You’ll think back to the times when you were out with your friends, whooping it up, not giving a hoot about what Visa had to say about your actions. Soon enough, you’ll start justifying ramping the lifestyle back up by telling yourself that you’ll get a raise, and with the extra money, you can pay off the debt. Hello, hedonic treadmill. Instead, what you need to do is to set target numbers and create little celebrations around them. When we were paying off the credit card debt, we’d treat ourselves to BW-3 wings and beer for every $2,500 that went away. When we were paying off the mortgage, we’d do a celebratory whoop or grab a beer at Beer Run when we knocked $25,000 off the principal. Just don’t set the milestones too low or make the planned celebrations too expensive. You’re seeking to acknowledge and celebrate the milestone and then move on, not treat it as if you won the World Series. (In your ReadyForZero plan, you’ll be notified automatically of some important milestones such as 25% paid off)
  • Work to move your “graduation date” up.  When I was pushing toward my goal, I did a lot of extra things to make extra payments. I taught at Kaplan. I bought items from the University of Virginia surplus auction and then sold them on eBay (I should coin the term “government inefficiency arbitrage”). I sold extra things around the apartment. Whatever it was, if I could get paid to do it while not failing out of school, I did it. And believe me, it helped. Seeing the impact your extra work is having will encourage you to keep going. Find a side gig. Do handyman work on the weekend. Whatever it is you need to do, move that date up, and track how much more your work is helping the situation.
  • Automate so that you don’t have to think about it. I’m not surprising anyone by saying that debt can be frustrating and stressful. It can cause you to dwell and linger on it for way more than is necessary or is productive. So, the less you can think about money, the better your life will be, and the more you can focus on the tasks which will help you to get to the finish line as soon as possible. Set up automatic payments to your accounts, when possible. (Apps like ReadyForZero can help you in that process)
  • Find an “accountabilibuddy”. You want someone who can both be a sympathetic shoulder (“I know this is hard”) and will still hold you accountable (“but you have to pay off $200 more this month!”). It takes a lot of mental fortitude to knock this out yourself, and even if you’re married, it can sometimes become an echo chamber. Instead, find a trusted outside party to provide you with equal amounts of carrot and stick, or, as I call it, hard love.
  • Remember, if you have a plan and stick to it, this too shall pass. Let’s say that it’s going to take five years to pay down your credit card debt. Think about five years ago from today. Doesn’t seem that far away, does it? Time will pass. You will survive. Just keep at it, and you’ll get there. There are lots of us who have emerged on the other side who are completely debt free who can verify that, while it stinks, you don’t die trying!

To quote Forrest Griffin, “the juice is worth the squeeze.” Getting to the point where you have finally put debt in the rearview mirror is the best financial feeling you will ever have. It’s a tonic for the soul. Hopefully you’ll find the advice from my own life helpful on your journey.


A message from Jason:  So what do you do once you become debt free? I’ve developed a course called “Winning With Money” that replicates 95% of what I do with my clients in our financial planning engagements. From budgeting to raising children to figuring out how much you need to retire, this course has 20 lessons and 8 worksheets designed to help you plot a course for financial security and certainty in the road ahead once you reach your “graduation date.”

I’m offering ReadyForZero readers a $50 off coupon through October 20 just by clicking the link below. If you’re not ready to commit, I have an alternative course that you can take for free while you’re working on your ReadyForZero plan.

You can click here to get information about the course. The discount will be applied at checkout in PayPal.

is a candidate for the CFP(R) Board’s certification, is a Series 65 securities license holder, and owns Hull Financial Planning. He is also a personal finance columnist for U.S. News & World Report.

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  • I totally agree that putting those interim steps in is as important as the long term goal. Without a map, you will never reach the destination.

    • “A journey of a thousand miles begins with a single step.” – Lao Tzu

      That was a popular phrase in the military. It was meant to keep us from analysis paralysis. However, I had one company commander, Scott Cunningham, who had a phrase one better, which was something like “Don’t step into something until you know how you’re going to step out of it,” meaning that unless you knew where you were going and how you were going to get there, it was possible to end up on a meandering journey, going from random step to random step without ever really getting there. That’s why you need those interim steps. You need to know how to know that you’re making progress; otherwise, you’ll put yourself at risk for regressing!

  • Tara

    Thanks for this post, Jason! For those of us in a *lot* of debt, it certainly is frustrating to not see the finish line. I agree that interim goals are the perfect way to do that. I also love the idea of these little celebrations. I think I’ll have to start incorporating that into my own plan.

    • Tara–glad that you liked it! If you don’t have those rewards along the way, then it’s really easy to revert back to the behaviors that led to the debt in the first place. You have to tell your limbic system (Monkey Brain, as I call it) that paying off debt is fun…OK…sort of fun…OK…not horrible. By having those rewards and goals along the way to look forward to, then it’s easier to fight off the temptation to buy a 183″ flat screen TV for the man cave. It doesn’t have to be anything crazy, either. Make it an *experience* instead, as we get more out of experiences than we do out of stuff.

  • Stapler Confessions

    The little steps are so important! For that reason, having a constellation of student loans was a benefit to us because we can pick them off one at a time and see the monthly payments disappear altogether. Although, I have to admit that I did a celebratory dance every month that we made a big payment. That feeling, in and of itself, was a great reward!

    • I was the same way until I consolidated them all. Then it seemed like a bigger mountain, which is why I set up the interim milestones. Otherwise, Monkey Brain will get in the way, tell you that you’ll never pay them off, or that you’ll only pay them off in 10 years, so you might as well have fun now.

      Having reached the other side of the journey, I can attest to how much better it is when you can pay for things with money you already have in the bank and ALLOCATED to that spending without needing to worry about what you’re skipping out on to do so. It certainly tears down a wall of worry.