(You’ve stumbled upon a long, gratuitous, reflective post that I write every year on my birthday. This is my 14th year. It’s really for my own personal archive, but if you’re curious: happy reading!)

Well, here we are, folks. The last year of my 20s. Wow.

As I always do before I write my annual birthday post, I go back and read through the posts of years past. Reading Twenty Eight, I seriously considered copy and pasting a lot of it. It’s kind of frightening how true it still rings. But on the flip side, it’s kind of comforting - the fact that the major themes in my life are staying pretty consistent from year to year means I’ve found a bit of a groove/niche/mission and that I’ve been able to hone and tweak it over the years to become more focused and more incorporated into my life.

This year was my 10th high school reunion. It was a huge factor in making me realize “Wow, it’s been an entire decade since that thing that feels like yesterday!” which turned into a common refrain over the course of the year. I guess I hadn’t really internalized how much time has passed since these milestones that still feel so recent. Going back to Ithaca or spending time with people I hadn’t seen since high school prompted me to look back and have a snapshot of the person I was when I was in that phase of my life.

I went up to Cornell a few weeks ago to be a guest speaker at a course on entrepreneurship. I’ve been invited to panels and group discussions at Cornell in the past, but this was my first time speaking solo - for an entire 50 minute class! Before class, I snagged a few minutes to catch up with Deb, who runs part of the Entrepreneurship@Cornell program. I met her my freshman year when I began working in the Eship office (which was my primary campus job for all four years and a huge part of why I have my career today!), so she got to know me pretty well. As we were chatting she brought up how surprised she was that I would be speaking at the class solo. She reminded me of how shy and quiet I was as a freshman. And she was right. I’d totally forgotten. Not even in my wildest imagination would I have expected to be standing in front of a class of 60 students giving a guest lecture anywhere, let alone back at Cornell.

There are so many aspects of my personality that have grown by leaps and bounds since I was in college (or even younger). Things like public speaking or, hell, sometimes even speaking in general. But it’s also been really fascinating to look back and realize how many aspects of my personality were so engrained even then. Before I even knew they would turn into the things that make me “me” or the things that make me good at certain parts of my job because they’ve been weird quirks I’ve had all along. It makes me kind of excited to see what I have to say about my current self 10 years from now.

On my 28th birthday, I had literally no idea what the year ahead would have in store. I’d recently gotten back from a few months in Southeast Asia, had an upcoming trip planned to South Africa, and that’s about as far ahead as I’d thought. Reality hit soon after, though. I was still living at the shore in my mom’s house, slowly but surely eating away at my savings, and wracking my brains for how I could turn travel into something that’s part of my life, not something I do between gigs. I had some ideas, but none that would turn into a sustainable lifestyle in the near future.

Luckily, in the ensuing months, I was serendipitously connected with a consulting opportunity that turned into a full-time job. I moved back to NYC, found a great apartment, bought all new furniture, and settled back into a “grounded” life. I kept a lot of the principles and lifestyle choices that had become important to me over the last year: a minimalist approach to “things.” I keep my tchotchkes to a minimum. I still keep a capsule wardrobe. I still value spending money on experiences over objects.

That was basically my life until July. I expected that was the life I would be living for at least the next 2-3 years. I’d come to terms with not being able to travel as frequently and living a “normal” life with a “normal” job. There was something reassuring about that. Until I was laid off. Then it was panic mode. I covered that already, so I won’t rehash it here, but in the end I came back to where I always do: I want to live an independent life. I don’t want to work in an office 10-6 every single day with the occasional holiday or vacation. It’s just not in my nature. It’s not what I want out of life.

I came to the realization that I’d been confusing my goal of running my own business with needing to build my own tech startup. Only recently did I accept there are lots of businesses in this world that aren’t tech startups and that doesn’t make them any less cool. I come from entrepreneurial stock. I’m not designed to follow someone else’s plan. Maybe at a later point in my life, but certainly not right now.

Part of this decision comes from 2 “heuristics” I’ve been using over the course of this year to guide my decisions in life and work: the first I learned from one of the women who started Kandu who I was so fortunate to work with: “Am I going against my natural tendencies?” While you could argue it’s good to go against your natural tendencies sometimes (in order to get out of your comfort zone), I think when it comes to your career, you’ll likely be better off if you continue to play to your strengths. I’ve learned a lot about what my strengths and weaknesses are on a deeper level this year and I’m so thankful for that.

The second is simpler: “Will I regret not taking this particular path in 10 years?” I’ve been using this one a lot lately, especially when it comes to evaluating opportunities for full-time positions that look really interesting and promising and comfortable against the rollercoaster that is self-employment. The answer, every time, has been “I will regret it if I don’t continue down the path of self-employment and see where it leads me.” It’s something I need to do and it’s something that I think ultimately will be the best path for me. I’ve been consulting full-time for about 2.5 months now and I wouldn’t want it any other way.

These heuristics have also led me toward easing up on my vegetarian diet. I’d been vegetarian for about 2.5 years and while my stomach has been a lot happier during that time, it wasn’t really making my life measurably better. In fact, it was causing more stress than good. I always ended up eating things that weren’t the healthiest choice because they happened to be the vegetarian choice. I decided to listen to my body (which was telling me I wanted a piece of chicken for months) and re-introduce animal proteins. It’s been a welcomed change from always feeling so “off” from not getting enough protein. I still don’t really enjoy that I’m contributing to the factory farm nonsense, but I do what I can.

One of the last recurring sentiments of this year has been that, for the first time, I feel fully entrenched in “adulthood.” For the last few years I felt like I was toeing the line. When I was around college students or people in their early 20s, I felt like I was still in some ways a part of that group. That feeling is completely gone. Now, when I’m around that age group, there’s an appreciable difference. It’s OK though, I’m definitely still a kid at heart and that’s all that matters. In fact, to celebrate my birthday, I’m going apple picking followed by winning lots of tickets at arcade games on the boardwalk. #29goingon9

All of this has come together to make me think a little bit more long-term than I have in the past. I used to operate by looking ahead at most to the next 2 months. I’ve started to appreciate longer-term thinking over this past year and, especially when it comes to building my consulting practice, I realize that I need to think ahead 6+ months to be able to make substantial progress and see the fruits of my labor. It’s been a nice change, really. Putting the goal post out a little further makes the little decisions along the way just that much easier.

Which leaves me with my annual review of goals. These are the goals I set for myself last year:

  • Support myself through work that involves consistent travel or living abroad. Had a small hiccup with this one, but back on track!
  • Integrate improved health and fitness into my everyday life. I actually did really well with this one for a good part of the year. Only recently did I cancel my gym membership and trainer because I can't reliably predict when I'll be in NYC. I still try to make good choices, but I'll need to figure out a good long-term solution.
  • Improve how I develop and sustain relationships when distance is involved. I was pretty stationary for about 6 months, so that helped. I've tried to stay as communicative as possible using the wonders of technology, but it is tough to maintain relationships when you have an unpredictable schedule so you can't coordinate meeting up, etc. Still a work in progress.
  • Dating: The whole being single thing is getting old. Yes, I move around a lot, but that’s not an excuse. See above excuse. Things were slightly better this year but still not awesome. Work in progress.

And goals for this coming year:

  • Support myself through location-independent/remote work.
  • Balance work and travel. Visit at least 1-2 new countries. Maybe try living in a different city for a while.
  • Figure out my "home base" for the next 2-3 years. I've been toying with the idea of moving out of the city to decrease my monthly expenses and increase my travel budget.
  • Better manage my health and fitness. Find a way to stay fit while on the road. Perhaps pick up running even though I hate it.
  • A slightly different take on managing relationships: It turns out that a lot of my friends are now outside of NYC. Some still in the general area, but others all over the world. I'd like to be better at making time/effort to see them in person more often.
  • Continued efforts on the dating front
  • Some other, smaller goals that I'm posting on Accompl.sh.

Just a few years ago the idea of turning 30 felt like it was eons away. Now the countdown is on. Part of me is ready for it, more than ever. I’m comfortable in my adulthood and probably more comfortable with myself than at any other point in my life, so it seems like a good time to reach 30. And from what I hear, your 30s are pretty awesome. But I’m not going to rush it. I’m going to savor every last moment of my 20s.

Now if you’ll excuse me, I have to go pick apples.


Past Birthday Posts: 28, 27, 26,25, 24, 23, 22, 21, 20, 19 (lost), 18, 17 (lost), 16