When I was 18, I thought the biggest measure of success was an editorial byline. If I could secure articles with cool publications, I’d be considered a good writer. At 21, I was obsessed with the idea of moving out of home, finding a boyfriend and traversing Europe. At 23, I wanted to start my own business and take a leap of faith. I’ve since accomplished all these things that I thought would make me complete, and yet here I am at 26 with an even longer list of ‘milestones’ to hit next.
I should know by now that even the most perfected plans for my future will be rewritten countless times. All of the proverbial checkboxes we imagine ourselves to reach are rarely seamless, all-encompassing or everlasting. And that pressure we feel to ‘achieve’ can obliterate the magic in the journey.
The phenomenon can be referred to as ‘milestone anxiety’ — a term coined to describe the stress-y itch one feels to tick off Big Life Things in order to be fulfilled, happy, and deemed successful. In the context of this article, I’m fixated on the mid-to-late 20’s and the early 30’s angst that tends to follow a very clichéd narrative. These are the years that we’re in a constant state of tug-of-war with what all-important chapter to enter next, especially as women.
Is it a move abroad in our 20’s like Mel Robbins mandates? Do we strive for home-ownership? Is self-sacrificing to run a self-funded business the way to go? Maybe a ring and a wedding and a slew of other tactfully paraded events? Is the biological clock ticking? You get the gist.
"All of the proverbial checkboxes we imagine ourselves to reach are rarely seamless, all-encompassing or everlasting. And that pressure we feel to ‘achieve’ can obliterate the magic in the journey."
I spoke to EFT therapist Natalie Claire King about why milestone anxiety is so prevalent today. With social media persistently showcasing the highlight reels of our peers, friends, and idols, I wanted to know whether it’s possible to refrain from comparison — both within our inner circles and broader societal pressures. According to King, it’s “not easy”.
“We live in a wild world where so much is shared and at the same time, a lot of the more vulnerable parts of our lives are kept offline. When we’re scrolling, we’re taking in a heavy dose of people’s positive moments, celebrations and achievements because they’re fun to share and engage in, so why not! But it’s helpful to keep in mind that life isn’t meant to be smooth sailing and even celebrities get served their plate of tough times.”
So, when navigating our next move through life’s trajectory, how can we know that what we're doing is for ourselves, rather than for the sake of external validation or approval? King prompts us to question, “does it make you happy? Does it light you up?”
I’m seriously contemplating getting a dog with my partner — a fluffy entity to elevate my long-term relationship and turn us into quasi-parents, forcing me to care for and devote myself to something totally outside of myself. We’re also saving for a new home, even though we’re comfortable with the current one we’re in.
I wonder why I am so fixated on these attainments when our living situation and general circumstances are cosy, but not primed for a chaotic little child-simulator to be thrown into the mix. When I ask myself “why” I really want this dog or the next abode, I know it stems from something deeper: binding us irrevocably together, giving us a shared purpose, and showing this to the world. I’m beyond excited for these plans, but I’m trying to get better at having conscious ‘check-ins’ with myself before making life-altering decisions.
King echoes this, suggesting we start getting curious about where these desires are actually coming from.“When you tune in and strip away what others will think — family, friends, co-workers, even that d-bag ex you secretly still want to impress — what are you left with? If it’s a calm, grounded pull, it’s a green light. But if it’s a panicked, ‘this will make me worthy’ spiral, slow down. That path leads to a never-ending cycle of people-pleasing.”
There is no guarantee of hitting life’s milestones, or the anticipated dopamine hit from reaching them. It makes me think the ‘in between’ bits are the really important ones. I’m not diminishing the power of our ambitions or the magnitude of hope, I’m just suggesting the “I’ve made it” goalpost is always going to keep moving, so finding peace in the gaps must be what matters most.
CEO of Kic Laura Henshaw knows this feeling all too well, and has most-recently been bravely vocal in her own personal debate as to whether to have children one day. It’s been so refreshing to hear someone speak up on a deeply personal conundrum that society says should have a definitive answer. I wanted to know Henshaw’s take on milestone anxiety, and whether it affected someone as objectively successful as herself.
"I’m not diminishing the power of our ambitions or the magnitude of hope, I’m just suggesting the “I’ve made it” goalpost is always going to keep moving, so finding peace in the gaps must be what matters most."
“By chasing society’s definition of success, we’re often setting ourselves up for failure or disappointment, as it disables us from tuning into the path that truly feels right for us, losing sight of what we genuinely desire. When it comes to the end of our lives, your promotion, or the age you got married (or didn’t), or whether you were renting or owning a home won’t be in your eulogy,” she says.
“When you think about our biggest milestones, most of them are just fleeting moments in time. Yes, you might feel fulfillment or joy in the moment, but then it wears off and you move straight onto the next thing (like needing a bigger house for example).”
If our benchmark for happiness keeps moving, we’re never going to experience sustainable contentment. There is no flag-on-the-moon moment that declares our victory in the Game of Life. Maybe it’s better to focus on the root causes of our anxieties, rather than always yearning for more.
Arielle Thomas (host of Process podcast and founder of Remy) is in her early 30s and recently decided to freeze her eggs. While reflecting on her own experience grappling with milestone anxiety, Thomas has had the same epiphanies as me, albeit different worries.
“I realised recently that the milestone anxiety was paired with expectations. The expectations that I had for myself, when I day dreamed about life as a teenager, what my loved ones expect of me and what milestones my own friends are moving through. The only measure is my happiness and gut feeling at this moment. I can set goals and make plans for the future, but I tell myself they're fluid because inevitably, things change.”
Our head noise is hard to control. Thomas and her friends share the “whiplash” of being told women “can have it all.” only to reach their 30s and see a reality that isn’t so simple. She says detaching from expectations makes it more manageable.
Bel Hawkins, writer and co-author of Make it Make Sense, can empathise. She reached a milestone I dream of: publishing a book that grapples with niche issues like this one (for the girls). Yet, she felt anxious when it came out.
"All of our envisioned milestones are powerful propellants forward, but if we are always chasing the next high, we’re unlikely to feel satisfied for long within."
“Everyone is so excited for you and acts like you've 'made it,' but I found the experience really anxiety-inducing and vulnerable, even though I'd been through it before. It's an incredible achievement, absolutely, and something I'm really proud of, but I was quite taken aback by how many times the first question I'd be asked was - what next? It was like — what about right now?”
Here I was, thinking this must be the pinnacle of a writing career that would bring me all-consuming joy. Turns out, I’m comparing myself to Hawkins' ‘milestone’ achievement without even considering what anxieties it could stir.
“I didn't take those interrogations personally ('what next?' 'Surely you'll find a husband now?' 'children soon?', but it was more of a reminder to me to celebrate things that are a really big deal for me personally.”
When that grizzly beast of comparison roars within us, Hawkins suggests practising introspection and getting to the root of the icky feelings to ultimately grow resistant to them. “I try really hard to do this for lower-stakes things in my life, too, like getting my residency card in Portugal, small wins I have running my creative studio, or honestly, friendships that mean a lot to me. Consciously detaching from that pressure was a real game-changer because it helped me trust my intuition a lot more.”
All of our envisioned milestones are powerful propellants forward, but if we are always chasing the next high, we’re unlikely to feel satisfied for long within. Exercising gratitude for what we have right now (and longed for once upon a time) could be the antidote for perpetual gratification-hunting.
If I can rework my definition of ‘success’ to be: a calmed nervous system, freedom to work when and where I want, regular date nights, seeing my friends, daily movement, quality time with my mum, and living near the water, then I’m already living out my past self’s hopes.
I’ll leave you with a quote by career mentor Alison Larsen Rice from her “Little, Rich Life” manifesto — this stopped me in my doom scroll yesterday: “A Little, Rich Life is a life that’s small in size but deep in satisfaction. A life that is consciously contained. A life that can be lived into and enjoyed vs. planned and endured. A life that is void of comparison and abundant in self-determination.” This is the life I vow to live moving forward, free from an obsession with what comes next.
