From Graduation to Retirement: Why Progress Builds Confidence
FINANCIAL ADVICE | GUIDANCE | INSIGHTS | OBSERVATIONS
This year, my oldest child – my daughter Olivia – graduated from high school. It reminded me just how important it is to pause and celebrate milestones – whether it’s a graduation, retirement, or financial planning win.
Olivia has always been hardworking and determined: studying for AP classes and achieving a 4.0, participating in leadership, and pursuing her passion for dance. It’s absolutely amazing, and I always wondered if she’d ever take a moment to recognize how hard she worked and how much she’s accomplished.
I watched her shake hands with the principal, get a picture in front of the 675 kids she graduated with, and felt so much love and pride (and I’m sure that other parents who have experienced this moment know just what I mean).
But what really struck me was seeing her walk back down through the middle of all those students with a huge smile on her face. I could tell in that moment just how proud of herself she was. It was an incredible feeling.
A few days later, when I had a moment to reflect on the experience, I felt the same pride I had on the day itself, but I couldn’t help but to think, “How long will that feeling of accomplishment last for her?”
That question got me thinking – not just as a dad, but as a financial advisor. Because whether it’s a graduation or a retirement, I’ve watched many people attain something big and feel incredible pride, only to find that, sooner or later, the excitement fades and a new set of questions starts to take shape.
It leaves me wondering, “What creates the kind of confidence that lasts beyond that single moment of happiness?”
What actually makes people happy?
Why Big Achievements Alone Don’t Create Lasting Happiness
If you’ve ever reached a big goal – graduating, selling a business, paying off a mortgage – you know the feeling. That rush of satisfaction can be overwhelming in the best way.
But it doesn’t last forever.
A day later, or a week later, or maybe even just 10 minutes later, your mind inevitably starts to look ahead to the next challenge. Olivia accomplished a huge goal of graduating high school with a 4.0, but now she’s already thinking about the next chapter: going to Gonzaga and pursuing a very difficult degree.
And as a financial advisor, I’ve seen the same thing many times when my clients reach retirement. People work extremely hard to retire, achieve that goal, feel amazing, pat themselves on the back… and then before they know it, they’re back to feeling anxious or worried about the next question of whether they’re going to be able to stay retired.
The excitement of “arriving” fades faster than most of us expect.
What Actually Creates Lasting Confidence?
Over the years, I’ve come to believe something simple but powerful:
It’s not reaching the goal that creates lasting confidence. It’s seeing that you’re making progress.
Progress is a tangible thing – it’s the reassurance that you’re moving in the right direction, even if you haven’t crossed the finish line yet. Research shows that celebrating those small, consistent wins is one of the most effective ways to stay motivated and keep moving forward.
I think my daughter now looks forward to signing up for a whole new set of classes, taking them, and passing them semester by semester. She’ll be able to set goals, measure her progress, and feel proud of each milestone she reaches as she moves through college – because it’s not just about the final goal of getting her degree, it’s about the growth she’ll experience along the way.
That same philosophy has shaped how I approach financial planning and how I try to coach my clients. A financial journey isn’t just about hitting one big number. It’s about steadily improving, season after season, and knowing your effort is paying off. Just as importantly, it means taking the time to pat yourself on the back along the way and say, “Gosh dang it, I did it. Congratulations!”
How Can You Measure Your Financial Progress?
Another thing I’ve learned over the years as a financial advisor is that, a lot of the time, people have a hard time telling whether or not they’re on their way toward their financial goals.
Here are a few questions to help you gauge whether you’re moving in the right direction:
✅ Am I saving more this year than last year?
✅ Is my retirement income keeping up with inflation?
✅ Have I taken steps to reduce debt or improve my cash flow?
✅ Do I have a plan that adjusts when life changes?
✅ Am I regularly reviewing my progress with someone I trust?
If you can answer “yes” to even a few of these, you’re already on the path toward lasting confidence.
The Marathon Mindset: Why Financial Planning is a Lifelong Relationship
Watching Olivia graduate reminded me that life is full of milestones worth celebrating. But it’s also a series of chapters, each with its own challenges and opportunities.
Financial planning is a lot like that.
It isn’t something you do once and set aside. It’s a lifelong relationship with your goals, your values, and your confidence in what’s ahead.
When you see planning as a marathon instead of a sprint, you free yourself from the pressure to get everything perfect right away.
Dividing the big goal into parts gives you the space to celebrate the small wins along the way, and checking in regularly on things such as your insurance needs or emergency savings can help keep you on track and adjust your pace if needed.
That perspective can help you stay confident as you enter each new phase, including retirement itself.
Setting New Goals After Retirement
So what happens once you’ve “made it”? It’s a question more and more people are asking, especially after they’ve reached the big goal and stepped away from work. As Forbes notes, retirement can leave many feeling adrift, without a sense of purpose.
Because the truth is, retiring doesn’t mean you stop measuring progress. It just means the definition of progress changes.
Once you’ve made the transition, progress might look like confirming that the income you’re generating is enough to keep you retired, and that it’s increasing every year to help you keep pace with rising costs and inflation. It might look like being able to invest in things like travel or hobbies. Or, it might look like setting aside money for the next generation – perhaps to help your own kids or grandkids with their college dreams.
That’s why it’s so important to have a plan in place not just to reach retirement, but to stay retired – and to measure that progress regularly.
When you know your income is meeting your needs and growing over time, you can feel confident that the effort you put in to reach this point continues to pay off. And that confidence is worth celebrating just as much as any milestone along the way.
What Financial Milestones Are Worth Celebrating?
Whether you’re just starting out or already retired, here are some examples of progress worth acknowledging:
✅ Funding an emergency savings goal
✅ Paying off a credit card or loan
✅ Increasing your retirement contributions
✅ Meeting with your advisor to revisit your goals
✅ Supporting a cause that’s meaningful to your family
At the end of the day, these milestones are about more than numbers or checklists. Moments like these are reminders that you’re moving forward with intention, and while they may not come with a diploma or a standing ovation, every small step deserves recognition.
Watching Olivia’s pride at her graduation and excitement to move on to college has reminded me that progress isn’t just about achievement – it’s about taking a moment to appreciate how far you’ve come before moving on to what’s next.
Bringing It Back to What Matters Most
No matter where you are in your financial or life journey, knowing what progress looks like for you – and how to measure it – can make all the difference. Especially during uncertain times, celebrating each milestone can really bring life back into focus.
That’s definitely what Olivia’s graduation has done for me. As a parent, watching her grow into herself has been one of the great joys of my life. And, seeing her take pride in her progress reminded me why I’m so passionate about the work that I do.
Because at the end of the day, financial planning isn’t only about numbers.
I became a financial advisor to help people feel confident, so they can focus on what matters most: family, purpose, and the freedom to enjoy each new season.
Ready to Reflect on Your Own Progress?
If you’d like help measuring your milestones (and finding ways to celebrate them!), I’d love to connect. Let’s schedule some time to review your personal financial progress, so you can feel confident about what’s next.
Because whether you’re crossing a finish line or taking your first step, progress is always worth recognizing.
-
Sam Gullette
Sam Gullette, CFP®, CLU®
Certified Financial Planner™
‘My mission in life is to help people take control of their money and avoid financial stresses. My clients are successful professionals and executives, many of whom are compensated heavily with company stock. Together we design plans to help maximize their wealth-building opportunities, provide strategies to minimize taxes, and help make sure their family is well cared-for if life throws them a curveball.’