Allison Trowbridge, Author of Twenty-Two, On Life Lessons For Twentysomethings


By Crystal Tate

Ironically, writer and social entrepreneur Allison Trowbridge came up with the idea for her book, Twenty-Two: Letters to a Young Woman Searching for Meaning, when she was 22. “When I was graduating from college, I pulled an all nighter with one of my best friends in the spring of my senior year,” said Trowbridge. “We were talking about how it's such a unique moment in history to be a young woman and how there's never been more opportunity or access. I felt like there was so much pressure to have my life figured out, to figure out my dream job, find my dream guy, have a family, have a career and be perfect all the time and I mean this is even before all the social media pressures that exist today. And then also I'm supposed to solve global poverty by the time I'm 30 so it's like we have this education and these great opportunities, but also just this sense of we're not making the most of it. I felt a lot of the young people around me in the midst of that pressure and most people just disengage in life because they can't rise to all of those occasions. So I said to my friend ‘I wish there was a book called Twenty-Two that spoke to all the questions and uncertainties and opportunities’ [of life],” explained Trowbridge.

The Life Currency was anxious to learn more so we met with Trowbridge at a coffee shop in the Union Square neighborhood of New York City. Our meeting ran well over our scheduled time, and Trowbridge dropped numerous gems that we couldn’t wait to share with the TLC audience. Keep reading for Trowbridge’s advice on why it’s OK to not have your life figured out and so many more words of wisdom!

What advice would you give to a 22-year-old today, both life advice and career advice?

I'll start with life advice. Growing up, I always thought that one day I was going to arrive, that I was going to hit this end point, have my career established, figure out family life and become this adult and finished product. I figured it would probably happen around the time I was 35 or so and I had this vision of myself of this finished grown up product. The revelation for me in my 20s was that we never arrive. We never crossed some big finish line and hit an end point. If you live your life waiting for the next thing and waiting to get it figured out, you're going to miss your life. So I think those early 20s, all of the uncertainties and the not knowing, like that journey is your destination, to sit in all the questions and uncertainties and realize like we never get to tick all the boxes. You never just cross some finish line. Instead, just enjoy the process and take the pressure off a little bit. Even in college, I used to think that that choosing a major was like an airport where you choose your gate and take your flight and you're off and that's that. And even careers are much more like a road trip. You get to take the long route and scenic route and sometimes you feel like you're going off in the totally wrong direction but you're going to learn things from that that you're going to apply later on. When I was in my senior year of college, I was doing wedding planning on the weekends to be able to make ends meet and I did that for the first couple of years of my nonprofit work and I was like how do anti-slavery and weddings go together? But then I started planning these huge NGO (non-governmental organization) events, and I was like ‘Oh I know how to plan an event and create an experience’ and I learned that from wedding planning.

Careerwise, I would say you don't know how it's all going to work together so go after things that you either love and just make you light up or you enjoy the work so bring your best to it, but also take opportunities where you're going to learn something. Don't expect to get your dream job straight out of college. It's going to be something where you learn and take some wrong directions. But even if you have a terrible experience, there are so many lessons to be learned there. If you have a bad boss who doesn't treat you well, that's going to teach you so much about what it means to be a good manager someday. So rather than focus on having to have some perfect job, focus on what you're learning in that situation you're in and then work really hard at it because all the best opportunities I got came from just saying yes and being unafraid to do the grunt work. Doors would just open because I was constantly creating or innovating or just doing the work that other people didn't want to do and I was able to show leadership as a result of that.

What would you suggest to a young woman who isn’t sure about their passion or what they want to do?

For me, one of the best things I did was I took a role where I could try a lot of different things. In my first job out of college, I was the first employee in a brand new nonprofit so it was just the founders and me. And because of that, I literally did every single job that they didn't want to do. So everything that they thought was boring or grunt work, I did so I was able to learn what I enjoyed and what I was good at it. I got to try e-commerce, managing the financial systems, building the website, so I can step in and take on these roles if need be. It became clear really quick that I had a good knack for communication so I was able to focus on the communications in the organization as we grew and focused on the partnerships. Since I was able to do a lot of role, it actually allowed me to learn a lot about what I'm good at and what I'm not good at, and that became really a gift. If you're in a small business or a small organization, just try everything. If someone's like who wants to try running this whether it sounds fun or not, just try it and you'll get that experience. On the flip side, if you're in a really big company, that's actually a really great chance to learn from so many experts who are there. You're going to have people there who work in different departments doing all different kinds of roles and you're going to be exposed to a lot of different things so there's benefits to both. Just try things out.

Lastly, if you aren't passionate about the work, side hustle. Working in the NGO space was my side hustle when I was in college. I was just volunteering for this nonprofit and they asked me on full time but I didn’t have a plan to work in the nonprofit space. I thought I was going to law school. If you have a friend who is running a blog that you really like or have space to volunteer at a local organization you care about or get involved in your church, find those areas where you can just support something that you care about and that will be a great opportunity that will open doors as well.

You talked about wedding planning and working for a nonprofit as a side hustle in college. What suggestions would you give on having a side hustle in college, and what are the benefits to having one?

A concept that I came across recently that I think is so cool is a portfolio career. It's a term I've heard used a lot at Oxford [University] wher some people go for a very charted out career path. I know I want to make partner at the law firm and become a surgeon, and I'm just going to go step by step and it has a very clear career trajectory. But outside of those very clear trajectory professional roles, I think the world is changing so rapidly. Work is changing so rapidly. Opportunities are changing so quickly. So one of the best things you can do is be a generalist and learn how to specialize in different things, have different projects you're working on and different things you're passionate about. In the last couple of years, I've been working on a book, working on a documentary film, advising nonprofits and going back to school. It's not to say bury yourself and have too much going on. Be strategic about it and be thoughtful about what you care about and what you want to build into but technology is giving us so many opportunities to try different things and explore. Start a blog on a topic that you're passionate about or support a friend who's doing something really cool and figure out how you can create value for them. Even at most startups if you say ‘hey I just want to intern for a couple hours a week and just help you build what you're building because I believe in it’, people love that! So I think that this idea of a portfolio career takes the pressure off of having to have your career set and have one job that's your dream job and instead use this unique time in history where there's so much opportunity available to try different things and support different things you care about.

What's your advice to someone who wants a mentor or wondering if they need a mentor?

I think everyone needs a mentor, and I would actually say mentors. I think we put a lot of pressure around this idea that you need to find a mentor and it’s one person like it's a dating relationship. Instead I think it's much more informal and more that we need to make sure that wherever we're at in life that we always have people who are building into to us or mentoring us, those who are peers so we're like walking alongside and those that we're mentoring and building into. So you should always have all three dynamics to stay healthy in your personal growth. It's much more of an informal process so the women who have mentored me over the years, it was never some formalized ‘we're going to meet every two weeks for this long’ kind of thing. It's much more of we built a friendship and a relationship and they're further along in their journeys so they can give me guidance and build more into me. But I also think that the piece of advice I would give is always be thinking about how you can create value for that person as well. I never approach these [relationships] as ‘I'm just going to take from you.’ Don't write to someone ‘I just want to pick your brain.’ That just feels exhausting and like so much work. Instead, build a friendship and a relationship.

What are the top three life lessons you've learned from age 22 to now?

1) The journey is the destination. You don't arrive. That's been like the biggest game changer for me because it's allowed me to lean into the process and also it makes hard times better to go through to you because you realize what matters is the character that's formed in us and how we're learning how to love people along the way and it's not about these finish lines you cross because we put so much pressure on what we produce, then you produce those things and you're like ‘Oh wait what mattered was the process of being in grad school and not getting that degree.’

2) Everybody is making it up as they go. When we're in our early 20s, we look at everyone else and think they've all got it figured out and they've got it together. The reality is everyone at some point or another has just made it up as they went along to. If a man reads a job description and it's above his qualifications, he'll say ‘I can do that’ and still apply. A woman will self-select out. I think as women we need to realize you just have to rise to the occasion. Believe in yourself, believe that you're capable of it, push yourself and just try and take that leap. The worst thing that happens is you don't succeed and then you learn but also get some thick skin. It's not personal if someone doesn't hire you. I wish I'd known that at a younger age. It would have made some of the losses and the failures so much easier if I wasn't taking it personally or tying my worth or value to that.

3) Don't compare yourself to other people. It'll steal your joy. It'll suck the life out of you. I have this bad habit where I see someone else on Instagram and not only do I want their life, but I'm like ‘I could probably do it better than they're doing.’ The world doesn't need another one doing their life a better way. You have to think all I've been given is me and the life that I have and the opportunities, the skills, the relationships, all of that. If we spend our life wishing we could be someone else or look like someone else, you wish your whole life away. We also need to remember that's not the fullness of life. Those are just snapshots. That's the highlight reel. If you can realize the comparison game for what it is and just say I'm not playing, It frees you up to celebrate other people's successes genuinely and to also see that some of the people who look like they really have it together are actually some of the people who are hurting the most or feeling the most lonely or struggling in ways that the world doesn't see. And it also frees you up to live your life more fully because I'm not going to look like that person or have the career of that person and that's OK. Like I've got this set of colors to paint with and I'm just going to make the most of it and be thankful, be grateful and lead with gratitude instead of always wishing for something I don't have.

Crystal Tate is the editorial manager of The Life Currency, and a freelance editor, writer and stylist based in New York City. When she isn't sitting behind her laptop, she enjoys spending time with family and friends, traveling and inspiring young women to shatter glass ceilings. Follow her on Twitter at @CrystalDenise and see more of her work at