What It Means to be the “Successful” One Among Your Friends
Work + Life Balance

What It Means to be the “Successful” One Among Your Friends

by Kit Warchol
December 03, 2015
When you attend a liberal arts school and befriend aspiring writers, artists, and musicians, something happens after graduation: people don't move on to law firms or tech companies.
Instead, they take day jobs at bars or restaurants or freelance as production assistants on reality TV shows in the name of their passion, spending every free moment between shifts rehearsing with their band or painting in small corners of tiny studio apartments.

Unlike many of my friends, I don't have a clear creative calling. This isn’t so much self-deprecating as it is realistic—there will be no film deals, gallery shows, or record label contracts for me. Instead, I headed down a much more traditional career path than anyone I knew, much earlier on.  At 22, I took a full-time gig with benefits. And by 25—through sheer luck, honestly—I’d stumbled into the kind of job that paid so well, I could afford to shop exclusively at Whole Foods and drink $12 green juices every morning if I wanted.

By many standards, I’d made it. I’d actually find later when I was burnt out and creatively unfulfilled that I hadn’t. But at the time, expendable income felt both glamorous and unreal, and I was ready to treat myself.

Here's the problem with this scenario: none of my friends were there with me. Suddenly, I was the odd kid out who'd skipped ahead into a different tax bracket. We’ve talked about the importance of honesty when it comes to talking money with friends, but when you’ve lucked into financial stability, how do you make things fair for everyone? 


Going out is expensive regardless of how much you make in take home pay, and there are always better uses for that money anyway. My friends and I started meeting for 5 or 6pm drinks at our favorite places to save some cash. An unexpected upside was how quiet it often is at bars around that time, making it easier to converse and meet new people. We also embraced the "Girls Night In." Do the math: two $12 glasses of Malbec per person or a $20 bottle of Gamay split four ways? Whatever you manage to save by avoiding full-priced food and drinks can be socked away into your emergency fund, regardless of your financial standing.
It’s surprisingly easy to forget what it feels like to not know whether you’ll make rent, but it’s still all too real for some friends.


I didn’t hide my success. When I was promoted, we celebrated. But I was always careful about how I approached money with my friends.

You’re supposed to feel comfortable venting to those you love and vice versa, but no one wants to hear that you spent too much money splurging at J. Crew when they’re panicked about how to afford emergency car repairs. Be sensitive and listen. It’s surprisingly easy to forget what it feels like to not know whether you’ll make rent, but it’s still all too real for some friends. Go out of your way to empathize and relate to their experiences.


When friends and I went out to dinner, I took convenient opportunities to cover the bill. That’s not to say that I made a big to-do flashing my card at every outing. But if a friend came to the table miserable after an excruciating day at work, I’d treat. It turns out there are a multitude of reasons to celebrate besides professional successes. I once ordered a round of Cava to toast my friend’s dog not needing surgery. We love that little terrier.

On the flip side, I learned not to turn down a friend’s offer to pick up a round of drinks. It’s condescending to refuse because you’re afraid they can’t afford it. In fact, it’s actually none of your business. Trust that your friends understand their finances and accept their offers graciously.
Don’t give in to the temptation to spend money as a sign of affection. 


Money really isn’t everything. As the holidays roll around, you have more finances to treat your friends, which is a great thing. But chances are they’re not interested in—or comfortable with—you giving them an exorbitant Apple Watch (save that gift for Dad, maybe?). Avoid the temptation to spend money as a sign of affection. You can still treat friends to things they’d never buy themselves without overshadowing your good intentions with price tags. For my friends, I'd buy the Nars lipsticks in bold colors or pricey hand-poured candles that no one in her right mind (no matter her salary) would buy herself.  

And if your friends suggest a Secret Santa pool with a $20 cap on gifts? Enjoy the challenge of finding the perfect something for a limited sum. You can use the money saved to buy a gift for your grandmother.


Whether it’s my birthday in June or the eggnog open house I throw each December, I love hosting parties. Dinner parties. Costume parties. Brunch parties. You name it. I realized pretty early on that throwing an event was the perfect opportunity to treat my friends to great food and great wine without any awkwardness. As my salary went up, we all got to share in the wealth of expensive cheeses and high-end ingredients.

* * *

The dynamic shifted when I made the bold decision to walk from the “successful” career in favor of a more creative position and, inevitably, a pay cut. But my social circle continues to relate to each other as they always have: through an honest and realistic lens.

We talk openly with each other, and conversation sometimes turns to money. We help each other practice asking for raises or edit each other’s follow-up emails on jobs. But more often than not, we’d rather talk about what we read in this week’s The New Yorker, what films we want to catch, or, frankly, weird dudes on Tinder. And that’s why, regardless of creative or financial success, we’re friends in the first place.

Have you experienced this first-hand? What was it like being the most successful amongst your friends? How did you deal?