Advice for New Grads
by Caitlyn Driehorst, Hannah Farrow, and Chris Casale
Published: June 9, 2025
You live and you learn! This spring, families gather across the country for college graduation, as youngsters with barely-matured frontal lobes leave the final nest.
We gathered our team of financial advisors to reflect on who we had been when we were 22, and the money moves we’re proud of – and some pointers we’d pass along, if given access to a time machine.
Caitlyn Driehorst
I’d tell my 22-year-old self to…
Start a Roth IRA: I worked several jobs all through college and (accidentally?) maxed my 401(k) my first year out of college. But I never opened a Roth account, or any other investing account. My parents both have pension jobs and I think they didn’t know to suggest it to me, and besides, I was feisty and wanted to cover my own living expenses, to the extent that I could. If I’d invested $1,000 in the S&P 500 in June 2011, that would be worth ~$4,333 today (including reinvested dividends) – and who knows what it would be worth in the 2050s, when I retire. And had I concentrated on a post-tax Roth account versus a pre-tax 401(k), I would have locked in the lower tax rate of my earliest earning years.
Stop throwing money at your student loan: To my younger self, debt (of any kind, personal or financial) itched like a mosquito bite. As soon as I could, I started shoving every spare penny toward my student loans. In retrospect, the interest rate on that debt was low, I could afford my payments, and my federal loans qualified for generous terms. I would have done better hoarding the cash to reduce my borrowing in grad school, or investing the money instead.
I’d thank my 22-year-old self for…
My Briggs & Riley suitcase: In 2011, I paid $220 for my red carry-on suitcase – what felt like an impossible amount of money at a time when most of my shopping was at Forever 21. But the man at the store told me I’d have that bag my whole life, and he may end up being just about right. That suitcase has circumnavigated the globe, gone with me on endless work trips and countless weddings, and in 2021 when the zipper finally broke, Briggs & Riley fixed it for free under the lifetime guarantee. It’s still in fantastic shape and I use it almost every time I travel. Thanks for being classy, Young Caitlyn. And speaking of…
Spending on travel: A winery in the Republic of Georgia, hostels across Germany, the hotel in Trieste where my grandmother had lived in 1946 during my great-grandfather’s deployment: my last year of college had lots of travel – and I was so bad at it. I got lost in Hamburg after midnight, developed an ear infection in Berlin and an eye infection in Moscow, missed a flight in Barcelona, and generally spent a lot of time asking exasperated strangers, “Do you speak English?” I’m proud of my younger self for being so bold in the presence of so little capability; not only do I have wonderful memories of that time, but I got so many mistakes out of the way so that when I lived in London for six months later in grad school, I was a much more confident and capable traveler.
Chris Casale
I’d tell my 22-year-old self to…
Don't Sleep on Your Company Benefits: When I first started working, I thought I had it figured out: decent salary, the occasional bonus, and I was already splitting a two-bed apartment with two roommates (I don't miss that accordion wall). So, when I heard terms like “ESPP”, “HSA”, “RSU,” my brain said, “IDK.” I figured that stuff was optional and for the higher-ups. Turns out, I was leaving real money on the table. Those acronyms are often a big part of your compensation and I wish I had taken the time to learn what was actually being offered. At that time, a quick chat with HR or maybe even a financial advisor to help me understand these benefits could have made a huge difference.
Invest in something uncomfortable: Soon after college, I wanted to buy a multifamily property and get into real estate investing directly. But I held myself back with every excuse: it’s too expensive, I don’t know enough, nobody would want to rent from me. Looking back, I wish I had trusted that vision and taken the leap.
I’d thank my 22-year-old self for…
Investing in home hospitality: I’ve always been all about making space for good times, which is why I chose an apartment in DC with an amazing rooftop. I paid a bit more in rent for it, but honestly, it was totally worth it. Hosting dinners and casual hangouts up there made for some unforgettable moments. Those rooftop evenings weren’t just fun — they were where some of my best memories were made.
My Gym Membership: When I first started working, I wanted to get more into fitness—but I wasn’t too keen on dropping a bunch of cash on a pricey gym membership. So my now-wife and I struck a deal: if she landed a new job, I’d finally commit and sign up. A few months later, she got the job... and I had no excuse left. That simple deal ended up being one of the best decisions I’ve made. What started as a reluctant promise turned into an amazing community that I’m still a part of today.
Hannah Farrow
I’d tell my 22-year-old self to…
Play the long game with money and with time. You don’t need to optimize everything all at once. Early career is a beautiful, chaotic mix of figuring out who you are, what you want, and how you want to live. Make thoughtful financial decisions, yes, but don’t get so obsessed with being “perfect” at money that you miss the bigger picture. The freedom to try, to change your mind, to learn in real time. That's the real ROI in your 20s.
I’d thank my 22-year-old self for…
Not getting a dog. Spicy, I know, especially because I love dogs and grew up with one who was basically my soulmate. I even fostered a pup in my early 20s and seriously considered keeping her. But I didn’t. And I’m so grateful. Because not having that responsibility meant I could say yes to every last-minute weekend trip: I didn’t have to think about boarding costs or rushing home between meetings. I put my time and money into travel, relationships, and career moves that really mattered to me. I know I’ll have a dog again one day, probably a great one. But that version of “home” wasn’t right for me yet, and making space for other priorities was one of the best gifts I gave myself.
Buying a house before I felt “adult enough”. My nice older landlady unexpectedly needed to support her grown son so I was on a very unexpected apartment hunt with no notice. With a rental market replete with male MIT Ph.D students in dilapidated Cambridge apartment complexes, I couldn’t find a room to rent to replace what I had. I’d saved very very aggressively to have down payment money but didn’t feel “ready” to buy the house – until I literally needed to get a roof over my head. And I went ahead anyway, and that purchase turned into a fantastic investment, which is part luck and part me doing a good job – despite feeling unprepared.
Learn more about establishing a financial strategy with room to grow
Join us for the next session of our webinar, “Personal Finance 102.” You’ll leave the session with a better idea of where you’re at, and how to get where you want to go.
"These webinars are especially meaningful to me, as they provide a valuable platform to discuss financial education and other important topics that impact people’s daily lives. I always look forward to the conversations they spark."
-Chris Casale, financial advisor
We are not attorneys and this article is intended to be educational and informative, not legal advice. As we like to say, “This is where your research should begin, not end.”
Author: Caitlyn Driehorst , Chris Casale , Hannah Farrow
Date Published: 6/9/2025
