The twenties are formative years. For me, there was the thrill of newfound freedoms, of finishing the formal schooling experience. There was also the terror of wandering and wondering what comes afterwards. The career paths that I thought were set in college didn’t quite pan out. But that desperation led to trying many doors, and I was fortunate enough to find one that brought purpose and, more importantly, financial footing.
While that is not an uncommon experience, it doesn’t have to be a terrifying one. That’s the premise behind Twenty, a community started by Katie Kirsch to help young adults connect with mentors for career and life guidance. A girls’ nonprofit leader, former IDEO product designer and educator, Kirsch has set out to reimagine how future generations navigate their twenties and all the accompanying questions, fears, joys and wonders.
We recently spoke with Kirsch about her journey to Twenty and what she’s learned so far. This interview has been edited for clarity and brevity.
What’s the story behind Twenty?
Twenty was inspired by the massive gap between college and the real world. It’s as if we graduate from what society deems “the best four years of our lives”—where we have a built-in community, support system, and blueprint for success—and then enter a dark abyss.
When I graduated, I had no idea what to expect from the “real world.” Most of my friends similarly felt lost, stuck, and confused, no matter which path or job they took. There’s a lot we wish we could tell our 20-year-old selves. Twenty is the community we needed most throughout this “defining decade.”
How did you get into entrepreneurship?
I first stumbled into entrepreneurship through a love of teaching. As kids, my sister and I were huge Harry Potter fans, so we’d dress up and play Hogwarts. I would play Professor McGonagall, create a fake spell book and syllabus, and teach my sister everything from Potions to Defense Against the Dark Arts. I even gave her fake exams!
In all seriousness, mentorship played a huge role throughout my upbringing. In high school, I mentored middle schoolers. In college, I mentored high schoolers. I wanted to make a bigger impact in education but didn’t know how.
At Stanford, I stumbled upon the d.school and found my answer in human-centered design. I spent four years in this wildly creative environment, learning how to build new products, programs, and ventures. With a few friends on campus, I founded my first company—a girls’ leadership nonprofit—and have been engaged in startups and entrepreneurship ever since.
The website tagline is “crush your twenties.” What does that mean today?
It’s about discovering what’s possible, opening new doors in your life and career, and figuring out how to take your next leap with confidence and conviction.
There’s no right or wrong way to spend your twenties. It’s a deeply personal journey, where we each experience serendipitous twists and turns that bring us to unexpected places. We couldn’t have initially predicted many of our greatest moments or baked them into a five-year plan—they came from a mix of open-mindedness, luck, and meeting the right people at the right time.
While navigating your twenties has always been tricky, Gen Z has taken this chapter to a whole new level. They’re entrepreneurial at heart, restless in how they switch jobs, try new things, and carve their own unique career paths. Across TikTok, Substack, esports, and NFTs, the youngest generation can start their careers anywhere and make a living doing anything, which sounds inspiring but can actually be paralyzing. In this new future of work, Twenty helps young adults find the purpose, direction, and support they need to thrive.
How does Twenty work?
At Twenty, we’re building the go-to source of truth for twenty-somethings—a place to get real talk on the real world from people who were just in your shoes. Members can book 1:1 sessions with mentors across industries, text Twenty for career and life advice on the fly, join group workshops and events, and more.
Our goal is to meet young adults’ needs holistically. Through “Twenty Work,” members can get concrete advice on applying to grad school or growing their careers in product, startups, venture capital, consulting, banking, and more. On “Twenty Life,” members can explore more personal topics such as finding work-life balance, managing personal finances, overcoming imposter syndrome, and building healthy relationships.
We’ve heard that our community feels refreshingly authentic, honest, and relatable, whether you’re looking to discuss salary negotiations or long-distance relationships. It’s inspiring to see even our newest members taking the time to record lengthy videos and audio clips for their Twenty profiles, voicing their most pressing questions, fears, goals, and interests with our community.
What brings mentors into the program?
Our mentors are driven by altruism and the opportunity to give back, help others, and share what they know. They love meeting new people and emerge from Twenty sessions feeling as inspired, fulfilled, and energized as our members. Finally, they can directly, personally relate to our members—there’s a lot they wish they had known earlier in their twenties, too.
What success stories have you heard so far from members?
Many of our members feel at a crossroads in their lives and careers, and through Twenty, they’re figuring out both what they want and how to get there. We’ve heard a diverse array of success stories—from getting accepted into top MBA programs to launching companies, breaking into new industries, getting promoted, and moving coasts and countries.
What’s been the most surprising thing you’ve learned so far from Twenty?
When we first started Twenty, our hypothesis was that most of our members would be at the start of their twenties, newly entering the “adult world.” However, many are actually at the end of their twenties with just as many burning questions as the 21-year-olds.
It makes sense—the older we get, the more we discover both what we know and what we still have left to learn. Every time we answer one set of questions, a new set arises. This is part of the joy of growing up—we’ll never stop learning.
Right now, we’re focused on twenty-somethings, but many are asking, “When is Thirty going to come out?”
What’s one thing you would tell your 20-year-old self?
Your twenties are going to be dense and composed of many individual chapters of work and life. Take your time—you don’t have to figure out everything all at once. Ask a million questions, stay open to new opportunities and experiences, and enjoy the ride!