Meet a Backslider: Interview #2
Meet the Backsliders is an interview series I’m creating for anyone who’s ever wondered, “What if climbing the ladder isn’t the point?” Each interview explores how smart, driven people got tired of chasing success that didn’t feel like success and what happened when they decided to backslide on purpose.
Every Backslider featured here has shared their story with generosity and truth, in a Q&A format. Their words are their own (with light editing for tone and flow from yours truly) - with identifying details kept vague to honor privacy (when requested).
Meet Arden: content strategist, writer, podcaster, and new(ish) mom who has redefined what ambition looks like.
Once fueled by constant achievement, Arden Evenson is now channeling that drive into connection, creativity, and community.
I met Arden Evenson in 2021 when we were matched on Lunchclub, an app for professional networking. We hit it off on our shared value of “working enough” and have kept in touch as internet friends. My laptop still has a sticker she sent me that says “More time to do less.”
After repeated experiences with burnout at intense startups and agencies, Arden chose to stop chasing promotions. She now works around 20 hours a week as a consultant, is fiercely picky about her clients, and has found that letting go of the need for "full-time" role has actually increased her professional standing.
Read on as Arden discusses the identity shift of becoming a "backslider," why we need to imagine more options than the binary of success or failure, and how her life is now richer thanks to her commitment to work less.
Q1: Can you describe your history with ambition? Was there someone in your life who pushed you toward being ambitious in a certain way?
My mom always described me as being very self-motivated, even as a young child, but I do feel like there was this vibe of achievement and ambition always present in the world around me growing up - particularly in school. In second grade (in North Carolina public schools in the 90s) everyone took an academic assessment that determined whether you should place in a gifted program.
I tracked in something called the “Highly Academically Gifted” program, which meant I was bussed to a central elementary school with all the other kids who’d tested this way and we were learning fifth grade material starting in third grade.
I was told to be proud of this achievement and it taught me early on that it was good to be the best, to be at the front, to advance quickly. That’s what was rewarded, what was praised, and it was understood that being ambitious was the only way to set yourself up for success.
Q2: Was there a specific moment or breaking point that pushed you to think about how you defined success for yourself, or did it happen gradually?
There’s been a few key moments that led me to where I am today.
I worked at an intense early-stage startup in my mid-20s, and after a week of working 15+ hour days, I got an email from my boss that I’d “dropped the ball” on something. I was at my college roommate’s rehearsal dinner when I got that email, and the thing I dropped the ball on wasn’t even clearly my responsibility. I’d been thinking about leaving for awhile, but this was the final straw in my realizing that it didn’t matter how hard I worked or how much I did, it wasn’t going to be enough for them. And I was done giving. That was the first time I quit my job for freelancing.
A few years later, I went back to full-time work, driven in part by the belief that in order to be successful, I needed to have a “real job” and move up the ladder. This was at a comms agency and the culture was better than the startup, but the workload was still intense. I never felt like I could keep up, and even when I shared that I was overwhelmed, it wasn’t until I was sobbing in someone’s office that people took me seriously. I quit after a year on the same day I was going to be offered a promotion. It wasn’t about the pay or the title, the environment and high expectations weren’t going to change, so it wasn’t healthy for me to stay. I went back to independent work
Fast forward to 2020, I take a full-time role with one of my clients after my partner gets laid off because of COVID (someone should have benefits… lol). I love the people, I love the culture, I care about the mission. But even in an environment of kinder humans with an excellent boss, I’m burning out. There is still an expectation that people can get more done than is reasonable, and I don’t often feel appreciated for my hard work and expertise. When I left this job, I was ready to let go of the standard definition of success and my pursuit of titles and constant progress. There was more to life than work.
Q3: How did you decide what kind of work or environment you wanted instead?
By the third time I returned to independent consulting, I was finally willing to admit that is what made me happiest. What this looks like is: not working myself to death – or even full-time (I work around 20 hours a week), being picky about my clients and turning down work that didn’t pass the vibe check (even if money is good), and not falling into the trap of trying to build my own agency or “grow the business.”
The way I seek growth now is working on interesting problems, it’s about finding more efficient ways to serve my clients who are doing good work, it’s about expanding my network in authentic ways and finding ways to nurture those in my community. And at the end of the day, what the structure of this work really offers me… is more time and energy to the things I care most about outside of work.
Q4: What has been the hardest part about letting go of the climb — whether that was status, money, or identity? And is it a “one and done” letting go or something you have to let go of over and over?
I could definitely be making more money in a “full time” role – and when you’re living in New York and paying for childcare, you absolutely feel that!!! But I know what the tradeoffs are for that money – more stress, more overwhelm, less time and energy for things that bring me joy – and that isn’t worth it, even if money is tighter than it could be.
Because the identity shift had been in motion for me for awhile, that wasn’t a big transition – and if anything, it’s been fun to embrace and amplify the “work less” mindset. People know they can come to me for a pep talk about “you don’t need to work so hard.”
I hadn’t thought about status before, but I actually think my status has increased over the last few years. People see me as an expert with more diverse experiences because I work across several clients. And because I’m not overwhelmed by work, I’m able to make time for writing, posting, podcast guesting, speaking, and attending events which I don’t think I would have had the mental bandwidth for previously.
Q5: When that gremlin voice shows up — comparing yourself to old colleagues or your past self — how do you quiet it?
For me it’s less comparison to others / past self, and more about imagining a different world for myself where I make more than enough money and our family could worry less about our finances. This shows up the most with me perusing LinkedIn job postings that I know I could excel at.
But then I remind myself of the tradeoffs – which are even greater now that I have an 8-month old child. We have part-time childcare explicitly because I want to have time every day with my child and watch him grow. And sure, I could work at nights after bedtime to catch-up on things (and I do when I need to), but I don’t want my life to be only work+parenting+sleep.
Not having my kid in full-time care also means that I don’t feel pressure to spend every moment with him when he’s at home. This means I don’t feel guilty about spending a couple hours each weekend at a wine bar writing or missing the last hour before bedtime if I have evening plans (Note: this also requires having a very engaged partner) because I’m with him until 9:30am and reunited at 3:30pm everyday. So when I’m feeling antsy about finances, I have to remind myself that I’m just not willing to trade my low-stress, flexible, joy-filled life for more money.
Q6: What are you ambitious about these days, if not work? In other words, what has backsliding given you that the old version of success never could?
I’d have to say I’m most ambitious about connections these days. I’m able to show up for my friends, my community, my industry in ways I wouldn’t have had the time or energy for in a regular job.
Sometimes that just looks like spending time with my friends (something many new parents stop doing because there’s only time for work and caregiving), sometimes it looks like planning gatherings for people in fintech, sometimes it looks like running monthly business owners calls for working moms, sometimes it looks like taking time to write – whether about my fertility/motherhood journey or how I’ve built my “good enough” business – and hopefully inspire others. My life is richer because of my decisions to backslide, and I think that radiates out to those around me.
Q7: What would you say to someone who feels trapped in a high-pressure career but is scared to take a step back?
So often we think of things in binary terms. Either I can have a high-pressure career or I can work an easy unfulfilling low paying job. Either I can be incredibly successful or I can be disappointing and unproductive. But there are often many more realities in between these that are also true. Try to imagine more options. What else might be possible?
Q8: What did we miss? Anything else you’d like to share?
I think letting go of perfectionism is also an important part of backsliding and accepting that your 90% is still exceptional work!
If you’d like to learn more about Arden, visit fireflyadvising.com and find her on Substack at Mother May I?
Do you have your own story of intentionally backsliding? I’d love to hear it.
You might be in a season of intentional backsliding if:
You craved a career shift, did something about it, and now wrestle with feelings about walking away from a “good thing” especially “in this economy.” But ultimately feel like it’s a good thing!
You left the grind and feel positively about it
You’ve achieved what you thought you wanted - and now wonder… is this it?
You redirected your ambition toward other parts of your life: caregiving, health, rest, creativity, community
You’re not burned out yet, but you felt the edges fraying and you’re trying to choose a different path before the fire hits
You’re not alone and you’re not failing! You’re simply choosing to define success for yourself.
If you’d like to share your story for this Meet the Backsliders series, email me at lindsey(at)lindseylathrop.com.
I still plan on launching a small group coaching experience called The Intentional Backsliders Club, but instead of this fall, I’ll launch it in January 2026. It’s for people who are ready to think differently about success, value, and what matters right now.
I’m still shaping this coaching group, but here’s how I’m pretty sure it will be structured:
We’ll meet live on Zoom bi-weekly over 12 weeks (so 6 times)
It’ll be a small, supportive cohort of 8-12 people
Each week we’ll explore a major theme, like:
identity disruption (and potential loss of status)
fear of regret
financial & structural security
ambition redirection & enoughness
There will be time built in for self-reflection and community sharing
You’ll receive optional homework
I’ll provide light coaching during the live sessions
We’ll meet and learn from real Intentional Backsliders (I’m hoping to have them as guests)
If this sounds like something you’d be interested in, help me shape the idea!
If you’re not sure if this is for you, you’re welcome to email me at lindsey(at)lindseylathrop.com and we can sort it out.
And as always, I’m available for 1:1 coaching which you can learn all about here.
