I was the first in my family to go to college—and the first to rack up a ton of student debt. I started adult life already behind financially. And then I went into human services, working in nonprofits where the work was meaningful, but money was always tight. I’ve always worked hard—multiple jobs, long hours, and side gigs to bring extra money. 

My problem was that I spent money as fast as I made it—sometimes on things I needed, sometimes on things that made me feel better in the moment. I was great at working, not so great at planning or saving. I told myself I’d deal with it “later,” but later kept moving.

And I resisted using a financial planner. It felt like admitting failure. Or like something meant for people with more—more money, more stability, more assets. Not people like me. But approaching 60, with retirement on the horizon and a new chapter taking shape, I realized I didn’t want to guess or worry anymore. I wanted a plan. I wanted to feel steady. And I wanted to know that everything I’ve worked so hard for would actually support the life I’m building now.

Why I Finally Called a Financial Planner

The mental load was too much.

Even though I’m super organized in other areas of life, I was mentally juggling too many “what ifs” with my finances: What if I get sick and can’t work? What if I outlive my savings? What if I want to travel more or help my family out? There’s a difference between keeping track of your money and having a plan—and I was ready for a plan.

It’s not just about money—it’s about peace of mind.

I had a lot of anxiety about meeting with a financial planner. I felt like I should already know better. Well, the angst was wasted. We met virtually and our first meeting was surprisingly gentle. It wasn’t about judgment; it was about clarity. We looked at everything—my income, expenses, retirement accounts, assets, goals—and made decisions based on reality, not fear. For the first time, I actually have a roadmap.

A planner can see what you can’t.

I had a few “aha” moments. Like realizing where I was essentially taking losses by letting my money sit. Or that I could structure my withdrawals in a way that will reduce my future tax burden. A good planner doesn’t just crunch numbers—they show you what’s possible and give you several scenarios.

What I Gained From Working With a Financial Planner

A Retirement Plan That Actually Works for Me

Not some boilerplate model, but one that accounts for my unique situation—my health, my goals, my want to die with 0 assets; and the fact that I want to write, travel, and make things in retirement. We mapped out a plan with flexible milestones. It made everything feel less overwhelming. By the way, the book Die with Zero should be essential reading for everyone these days. I couldn’t put it down!

Confidence in My Day-to-Day Decisions

I now know exactly how much I can spend each month once I decide to cut back on working – and where I can adjust if I want to splurge on a trip or invest in something that brings me joy. That knowledge has made everyday budgeting (something I couldn’t even think about before) feel empowering rather than limiting.

Freedom from Shame and Procrastination

Talking about money used to trigger a mix of shame and avoidance. That might be related to growing up poor and not having any money to talk about. That’s a conversation for my therapist. Now? It’s just part of regular cyclical tasks. I meet with my planner twice a year, make any changes to income or expenses, and have them explain how my investments are doing. I’ve learned to check in with myself when I feel like going on a crazy little spending spree. The emotional weight is gone so logic usually wins.

FAQ: Working with a Financial Planner

Q1: What kind of financial planner should I look for?
Look for a fiduciary—someone legally obligated to act in your best interest. I went with a fee-only planner (not commission-based), which felt more transparent.

Q2: What if I feel embarrassed about where I am financially?
You’re not alone. Many of us have internalized shame around money. But financial planners have seen it all. A good one creates a safe, judgment-free space.

Q3: Can I afford one?
Many planners offer different models: hourly, flat fee, or subscription. It’s worth exploring options. Some even offer sliding scales or group workshops.

Q4: How do I find one?
Start by asking trusted friends, colleagues, or peers for recommendations—that’s how I found mine. You can also check directories like the National Association of Personal Financial Advisors (NAPFA.org) or the XY Planning Network, which focuses on fee-only planners who work with people at all income levels.