30 And Not Thriving


One year ago, sitting with two friends over lunch, I realized that I was exceptionally behind in my life compared to them. One was married and starting her own family, another had been promoted and put a downpayment on her first house. They were both in tenured jobs with high profile companies.

Going around the table sharing updates about our lives, I felt inadequate. My life felt messy and unpredictable; they had their shit together. The only major life update I had to share was that my long-term boyfriend of five years and I just renewed the lease on our apartment.

“When is he going to ask you to marry him already?” one friend pried, excitedly.

I intentionally stuffed a breadstick into my mouth, so I had time to articulate my answer.

“We’ve talked about marriage,” I said, trying not to sound defensive. “But we’re waiting for the right time.”

“There isn’t a right time — and it’s not like we’re getting any younger,” the other friend joked.

“We’re focusing on our finances this year,” I said, now anxiously shoveling pasta into my mouth, stress eating myself into a food coma so I didn’t have to answer any more questions.

Finances are tough to talk about, and felt especially so in front of my friends who don’t have to be frugal with every dime at this point in their lives.

“Do you ever wish you’d stayed at your old job?” one friend asked.

Two years earlier I made the spontaneous decision to quit my job in investor relations, a career I’d been working in for seven years, to explore a new path. I hit a breaking point one day sitting at my desk, cross-checking spreadsheets. I realized I was making a huge mistake investing my time into something I wasn’t even remotely passionate about.

The prospect of age and time is something I’d been consciously aware of since I turned thirty.

Kailey Buchanan


“I can’t imagine doing this every day for the rest of my life,” I admitted to a coworker in the kitchen one evening, pulling a late night at the office and gulping back my tenth cup of coffee.

“I know. But imagine the house you’ll be able to afford in a few years,” they said encouragingly.

It was true, I was making a good paycheck, but I was miserable. I couldn’t justify my happiness at the mercy of money anymore.

I shrugged in response to my friend’s question. “Sometimes I think it would be nice to have some security,” I admitted. “It was easier when things were more financially stable.”

“Especially at this point in our lives, right?” my friend agreed. “I mean, we’re all thirty now. It’s important to have stability, to know where our lives are going.”

I knew she didn’t mean for her words to come off as judgmental – but I still interpreted them that way.

The prospect of age and time is something I’d been consciously aware of since I turned thirty.

The day of my 30th birthday, I went to the grocery store to pick up a few things. Coincidentally in the checkout line, I saw a magazine with bold letters on the cover that read, “Thirty and Thriving.” The words were placed beside a picture of a fresh-faced, perfectly put-together woman, wearing a form-fitting dress and Gucci heels.

This woman didn’t emulate who I was. I was wearing scuffed Converse sneakers and Lululemon leggings. I was on day four of unwashed hair, which was pulled into a high ponytail on the top of my head (and contemplating going on day five). I was having a breakout of adult acne on my chin. I had to check my online bank account before walking into the store, to remind myself whether I’d been paid that Friday. There was a chance I had to pull an extra few dollars from my line of credit to make rent.

There, in the checkout line of the co-op, I had an epiphany: I was thirty, but I wasn’t thriving.

“It will probably be easier for him to move on, if you both decide you can’t save your relationship,” my therapist said. “It will likely be harder for you, since women have a timeline; a ticking clock.

Kailey Buchanan


From what I saw in this woman, and most of my friends, is that I should be accomplished with a stable career, and be working on a side hustle on top of it. I should be married with a family of my own, or at least thinking about when to start one. I should have my student loans and debts paid off, and own my own house. I should have time in the middle of my day to work out, and still look flawless with great, clean hair.

But none of these things are real for me, some not even on the near horizon. A constant reminder every day since, from everyone and everywhere.

Even the couples counsellor my boyfriend and I have been seeing for the past year doubted our future. We’d been trying to fix some of the issues in our relationship so we could work towards marriage (another reason why we were waiting for the right time).

“Do you feel like you’re working against a timeline?” the counsellor asked me during one of our sessions.

“A timeline?” I ask, genuinely puzzled.

My boyfriend and I were at a bad point in our relationship, very much on the rocks. We were discussing what would happen if we broke up: who would keep the apartment, who would get the magic bullet, if we’d be okay.

“It will probably be easier for him to move on, if you both decide you can’t save your relationship,” she said. “It will likely be harder for you, since women have a timeline; a ticking clock. I know you want to get married and have kids….” she harshly continued.

I sat motionless, red-faced.

“Isn’t it my choice when I want to do things in my life, and how I choose to do them?!” I said, just short of shouting.

This was my second epiphany.

For most of my life, I had let other people manage my expectations of who I was supposed to be, and what I was supposed to have accomplished at every point in my life. And I realized that it was only going to get worse unless I did something about it. Unless I stopped caring so much, constantly comparing myself to others. Unless I stopped giving a shit and started living up to my own standards.

Now, approaching my 31st birthday, I acknowledge that this has been a practice over the past year. I’m starting to appreciate the fact that though I may not necessarily be thriving in everyone else’s eyes, I’m doing okay.

I’m practicing being more kind to myself and accepting myself for who I am: a thirty-year-old, unmarried, semi-broke, dreamer, who doesn’t want to settle in a job or a life just because the money is good or because it will afford the opportunity to buy a house in the suburbs. I’m someone who is okay with some instability because I’m happy. I’ll probably change my career again sometime down the road because I’m still undecided and interested in everything. I don’t want to rush into marriage and am very aware that my ovaries are at their prime. But I’m not worried (yes, counsellor, there is a right time for everything: when I’m ready). I don’t own Gucci shoes, but I do know that not having a pair doesn’t define my worth or accomplishments.

Turning thirty doesn’t mean you have to have everything figured out. If anything, I’ve learned that it’s an invitation to be selfish, to do the things I want, and live the way I want. To be unapologetic for it.

I’m thirty and thriving, in my own right.




  1. Excellent writing, and so much insight ! Some people never figure it out! You’ve got it Kailey! It only took me 83 years!

  2. Guess what! You can live without high heels and play in the dirt (rose garden).
    You can look at the sky and love the sound of wind and rain on your windows. Most of what I love is free. My friends are funny, smart, rich and poor, and down to earth and fiercely loyal. Some have been married, divorced, widowed, or always single. We are all older now and none of those things define us. All of life is valuable and every life is unique.

  3. Reading this has been exceptionally helpful. I’m 29 years old and recently quit a reasonably comfortable salary job. However, after 4 years I was burnt out at the stake ( Social Work ). I decided to go back to school to major in Anthropology; a degree I was discouraged from pursuing by my family. I’m working two non-stressful part-time jobs and saving my money to start a community garden where I live. We all need to realize that the lives others have DO NOT have to match ours. Success looks different to every individual. 🙂 <3