Now you tell me it’s a personal finance retreat? That feels odd to me. Don’t money workshops usually happen in auditoriums (the pricey ones) or church basements (the free, but sales-pitchy ones)?
And should I really pay for a multi-day reminder to stop spending money?
Fine — maybe I registered for the Lola Retreat somewhat skeptical about the current state of money education. Still, I attended the event with an open mind earlier this spring.
Across the weekend, presenters led nine sessions covering everything from basic financial mechanics to the deeper questions about why and how people make big monetary decisions.
It was the Lola team’s second gathering, organized by personal finance bloggers Melanie Lockert and Emma Pattee.
With tickets priced at $425 (full disclosure: I received a discounted press pass covered by my employer), I braced for an audience that might be, how to put it… a few pay grades above me. Instead, I was glad to find a diverse mix of women: working, retired, self-employed, married, divorced, young, seasoned and everywhere between.
Below are a few insights I brought home from my first personal finance retreat.
1. Being Settled in Your Job or Family Life Doesn’t Mean You’re Confident About Money — So Stop Freaking Out That You Haven’t ‘Arrived’
If you’ve ever eyed a mentor or coworker and assumed they have everything in order, think again. From fresh grads to veteran execs, the questions were strikingly similar: Am I saving for the right priorities? Am I structuring my financial life properly? Is everyone else making the same mistakes I am?
Spoiler: They probably are.
Liz Gendreau, who writes as Chief Mom Officer, told a story that stuck with me: She was the family’s primary earner and studying for her MBA when her husband underwent what was expected to be a routine surgery with a short recovery. Instead, he landed in intensive care for a week and then needed extended rehab, which drained the household’s emergency savings.
Gendreau emphasized not only the necessity of having emergency funds, but also having a plan for how to use them. Along the way she — like many others — discovered that leaning on friends and family for help is a strength, not a failure.
2. It’s Easier to Have Real Money Conversations at a Smaller Gathering
It’s simple to disappear into the crowd at a large conference. The Lola Retreat limited attendees to around 60, and over two days of sessions and mingling I noticed the small size made it much easier to introduce myself and engage with others. Faces became familiar quickly, instead of being swallowed by a mass of strangers.
Even better: Approaching panelists and presenters was welcomed. Many of these professionals stuck around for an entire day or even the whole weekend.
If you’re an introvert hunting for finance events near you, opt for smaller meet-ups to boost your chances of building genuine connections. Just be aware that those more intimate gatherings often cost more.
3. You Might Think You’ve Heard Every Hack, but You Haven’t
At each Lola Retreat session I found myself jotting down names of tools, sites and apps that speakers and fellow attendees suggested.
My top pick: Undebt.it, which helps you map out a debt repayment strategy whether you prefer the avalanche approach, the snowball method, or a custom plan. After a full day of sessions, I sat in my hotel room with takeout in one hand and my laptop in the other, updating numbers and refining my debt payoff targets.
I have never been so driven to spend a Saturday night in front of a spreadsheet.
4. Even the Pros Are Constantly Improving Their Own Finances
Few things reassure me more about my own money habits than hearing how financial experts have stumbled — and then corrected course.
Kristin Wong, author of the new book “Get Money,” drew knowing chuckles when she flashed a slide illustrating the all-too-familiar “Oh Sh*t” cycle many of us experience after payday.
Paulette Perhach, widely known for a famously frank viral essay on emergency savings, lives in a tiny 175-square-foot apartment in pricey Seattle.
These authorities are continually tweaking their personal finances — and you can do the same.
5. Small Wins Matter — Celebrate Them
Among these women, no financial success was too modest to applaud and no achievement too large to acknowledge. Whether they’d paid off student loans, tackled mortgages, or survived monetary crises, those who made progress were celebrated across the board.
That collective cheering was motivating, and it accompanied me from New York City all the way back to Florida. Before everyone left at the retreat’s close, attendees swapped contact details to form small accountability pods beyond the event. People’s objectives vary, which is precisely why having a group to keep you on track is so valuable: The daily steps matter just as much as the end goal.
Not only do I feel genuinely inspired to advance my financial targets, but I also returned home resolved to be an even stronger supporter for others tackling major money challenges.
Lisa Rowan is a senior writer at Savinly.
