I’m turning 33 this week, and I’ve been reflecting on how my 20s shaped everything I have now — the freedom, the travel, the business, the life. I’ve spent over eight years traveling full time, built a multiple six-figure creator business, and designed a life where I work from anywhere with my husband and son. None of it was an accident. Every decision had a reason behind it.
Here are the five things I did in my 20s that I believe every aspiring digital nomad and online entrepreneur should know.
Take the Most Risks You Possibly Can
Your 20s are the lowest-stakes decade of your entire life to take big risks — even if it doesn’t feel that way. You have time to recover, flexibility without a mortgage or kids, and the energy to try, fail, and try again. I spent part of my 20s in corporate finance because it felt responsible, but I eventually took the risk of leaving with no guarantees — and that changed everything.
The question isn’t what if this doesn’t work? The question is what does my life look like in 10 years if I never try? The regret of inaction is so much heavier than the regret of a failed attempt. Take the risk while the cost of being wrong is still manageable.
Backpack the World
If there’s any way to travel in your 20s, do it — even scrappy, even just to one country that isn’t your own. I’ve now been to 69 countries, and travel did something to me that no book, course, or mentor ever could. It shattered every assumption I had about how life was supposed to look and showed me that I had the power to create my own path.
Backpacking teaches you resourcefulness, self-awareness, and how much bigger the world really is. The barriers most people face aren’t money or logistics — they’re fear and waiting for permission. Neither of those is actually real.
3. Do the Inner Work and Learn to Love Yourself
This is the one most people skip, and it’s the one that matters most. I spent a significant part of my 20s chasing external validation — job titles, Instagram numbers, travel highlight reels — and none of it made me feel okay on the inside. Loving yourself isn’t a personality trait you either have or don’t; it’s a daily practice and a decision.
Without this foundation, you won’t believe you deserve the risks, the money, or the freedom. If you carry toxic patterns within yourself, you’ll attract toxicity around you. Journaling, honest conversations, time alone — whatever it takes, start the inner work early, because the earlier you begin, the more of your life you get to live from that place.
4. Learn How Money Actually Works
Learning to make money is different from just making money — it’s about understanding the mechanics of income outside of trading your time for a salary. Nobody taught me this in school, and most of our parents didn’t know it either. The traditional model of get a job, get a paycheck, repeat until retirement works, but it’s not the model that creates freedom.
Learn about digital products, passive income, email lists, affiliate marketing, and how to sell something without feeling gross about it. Financial independence isn’t just about having money — it’s about having options. And that knowledge is more accessible now than it has ever been.
5. Start a Side Hustle
You don’t need to quit your job, write a business plan, or have it all figured out. Start something on the side while you still have a safety net, low stakes, and the energy to figure it out. A side hustle teaches you how to sell, how to market, and what it actually feels like to make money from something you built.
When I was in corporate finance, I was building quietly — testing ideas on lunch breaks, weekends, and after hours. That messy, imperfect process was the training ground for everything I’ve created since. You just need an idea to help one person and the willingness to start before you’re ready.
Ready to Build Your Online Business?
If points four and five hit you — if you know you want to build something but don’t know where to start — that’s exactly the conversation we have inside the Wanderlover Business Academy. I’ll walk you through building your niche, your offer, your content strategy, and your first sales system, from I have an idea to I have an actual income stream. Version 4.0 now includes an AI business coach to help you map your specific path.
Your 20s aren’t waiting for you to feel ready. Neither is your future. Start now — the link is in the description.
Read Next
The 5 Books That Have Changed My Life
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How to Attract Money for Wealth and Abundance
5 Life Principles I Live By as an Entrepreneur
Comparison is the Thief of Joy
How to Change Your Life in 6 Months
