I Spent a Weekend Talking Money With Strangers. Here’s What I Learned

If you tell me we’re going on a retreat, I’m going to picture trust falls in the woods. Outdoor yoga sessions. Campfire songs. I’m all about it, except for the trust falls.

Now you tell me it’s a personal finance retreat? This does not make sense to me. Don’t personal finance seminars take place in auditoriums (the expensive ones) and church basements (the free, but sales-pitchy ones)?

And should I really spend money on a multiple-day reminder to stop spending money?  

OK, maybe I signed up for the Lola Retreat feeling jaded about the state of personal finance education. But I ventured into the event with an open mind earlier this spring.

Over the weekend, speakers presented nine sessions that ranged from the how-tos of personal finance to the more complex elements, like the whys and hows of making big financial choices.

It was the second event from the Lola team, led by personal finance bloggers Melanie Lockert and Emma Pattee.

With tickets at $425 (full disclosure: I got a discounted press ticket that my employer paid for), I expected the crowd to be, how should we say?… at a pay-grade way above mine. But I was pleased to find a variety of women at the event: working, retired, self-employed, married, divorced, young, experienced and everything in between.

Here are a few takeaways from my first personal finance retreat.

1. Being Established in Your Career or Family Life Doesn’t Guarantee Financial Confidence, So Stop Panicking That You Haven’t ‘Made It’ Yet

If you’ve ever looked at a mentor or colleague and assumed they have it together, that may not be the case. From new college grads to seasoned executives, the questions were the same: Am I saving for the right things? Am I planning my financial life correctly? Is everyone else making the same mistakes as I am?

Spoiler alert: They definitely are.

Liz Gendreau, who blogs as Chief Mom Officer, shared a story that stayed with me: She was the breadwinner for her family and working on her MBA when her husband went into the hospital for a surgery that should have been routine, with a short recovery time. He ended up in intensive care for a week before a long rehabilitation process that drained the family’s emergency finances.

Gendreau stressed the importance not just of having money for emergencies, but having a plan for what to do, as well. Along the way, Gendreau, like so many others, realized asking for help from family and friends is a sign of strength, not a weakness.

2. It’s Easier to Talk About Money at a Smaller Event

It’s easy to get lost at a big conference or seminar. The Lola Retreat capped attendance at about 60, and over two days of sessions and networking, I realized the small group made me feel more comfortable introducing myself and connecting with attendees. Faces quickly became recognizable, instead of being lost in a sea of strangers.

Even better: Approaching speakers and panelists was encouraged. These professionals tended to stick around for a whole day, if not the whole weekend.

If you’re an introvert looking for personal finance events in your area, look for smaller ones for a better chance at making personal connections. But be warned that those more intimate events may come at a higher cost.

3. You May Think You Know All the Tricks, but You Don’t

During every session at the Lola Retreat, I found myself scribbling the names of tools, websites and apps that speakers and attendees recommended.

My favorite: Undebt.it, which helps you figure out a debt payoff plan whether you’re an avalanche fan or a snowballer, or you want a custom plan. After a whole day of Lola Retreat events, I found myself in my hotel room, eating takeout with one hand and crunching the numbers to get an updated picture of my debt and my payoff goals.

Never have I felt so motivated to sit in front of my computer on a Saturday night.

4. Even the Experts Are Still a Work in Progress

Nothing makes me feel better about my money than learning about how personal finance experts messed up — and then fixed their financial blunders.

Kristin Wong, author of the new book “Get Money,” drew knowing laughs when she showed a slide of the “Oh Sh*t” cycle so many of us go through after each payday.

Paulette Perhach, perhaps best known for a boldly titled viral essay on emergency funds, lives in a 175-square-foot apartment in uber-expensive Seattle.  

These experts are constantly refining their own finances. And so can you!

5. Wins Are Wins Are Wins

In this group of women, there was no financial success too small to celebrate and no win too big to recognize. Whether they’d conquered student loan debt, mortgages or financial emergencies, those who made it through to the other side were celebrated without exception.

That shared celebration was empowering, and it followed me from New York City all the way back to Florida. Before departing at the end of the retreat, attendees exchanged contact information to form small accountability groups beyond the conference. Everyone’s plans are different, which is the beauty of having a group to keep you accountable: The action steps are just as important as the final goal.  

Not only do I feel seriously encouraged to make major progress on my money goals, but I also came home determined to be an even better cheerleader for people facing big financial tasks.

Lisa Rowan is a senior writer at the Penny Hoarder.