5 Little Bets to Make in Your Twenties With Huge Upside

Find unexpected avenues and arrive at extraordinary outcomes

Happy Friday! 

I took a break from writing this week. 

The article you are about to read was published a little over a year ago. It's still a good one!

Why did I take this week off? 

I've been writing non-stop for well over a year, and I'm going through a promotion at work.

It felt like the right time. 

Here's a quick update on everything going on in my life—all good stuff!

• Passed the Ohio Health Insurance exam and getting bumped up at the start-up I work for called Beam. 

• On my third week of classes for Morning Brew's MB/A program. The COO of Athletic Greens, Kat Cole, taught last night's class. Her story and perspective literally flipped everything I thought I knew about leadership on its head. I hope to write about her soon. 

• Training for a marathon with my friend Jonathon. Not easy getting up at 7 am on a Saturday to run 18 miles. Jonathon and I call this the year of grit. There's value in building grit. Every time we run, I feel as if I'm expanding the perimeter of my willpower.

I need a favor. 

I want to improve Yo Pro Library, but I need your help. 

Email me the answers to these two questions as honestly and quickly as you can. A little feedback goes a long way. 

1.) If you run a newsletter, what would you write about? 

2.) What length articles do you like to read? 

a.) Short quick burst of information. Gets to the point. 

b.) Long-form. 1,800 words. Something I can dig into. 

Talk to everyone next week! 

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5 Little Bets to Make in Your Twenties With Huge Upside

Our twenties are a series of little bets.

We follow what excites us, practice new skills, try new things, and note the audience’s reaction. Some things stick; most fall flat. Either way, we learn something about ourselves and let that guide our next decision.

The writer Peter Sims introduced the idea of little bets in his book by the same name. He demonstrated that innovators like Steve Jobs, Frank Gehry, and Chris Rock didn’t start with a big idea or plan out an entire project in advance. “They made a methodical series of little bets about what might be a good direction, learning critical information from lots of little failures.”

A feedback loop allowing them to “find unexpected avenues and arrive at extraordinary outcomes.”

Our twenties are an excellent opportunity to take chances! Use the time to test and probe for new angles and breakthroughs, even if that means risking failure.

If you’re having trouble finding a bet, here are a few ideas to get you started.

1. Create a social media account for a hobby or your career

Putting your work in front of an audience is TERRIFYING.

I remember the butterflies in the pit of my stomach after my first career-related Instagram post. To submit your work to the universe is to subject yourself to critics — that quality never goes away. However, the butterflies dissipate. Like jumping into a cold pool, your mind adapts, and you get used to it.

The upside of this little bet can change your life. You learn more about your hobby or career from people who share the same interests, and you become an expert on personal branding: a skill that carries over into anything you decide to pursue later.

Start small. Create an account on Instagram and take one photo of yourself engaged in your hobby or career. Next, provide some context in the caption or give a tip that people can use today. Post once a week for three months and build from there.

After three months, you might discover that you’re not as passionate about the subject as you thought. That’s ok!

If the bet doesn’t pay off, the skills you picked up will follow you wherever you go.

2. Do your research and pick an investment play

I’m not talking about a get-rich-quick scheme, I’m talking about doing some homework and investing money towards something meaningful.

I’m not a big stock guy, but I put a small portion of my earnings in Tesla. And no, it’s not because Morning Brew said I should. I spent months researching the company: scouring articles, studying their technology, researching financial projections. I even read Elon’s biography and wrote a book review for my blog. I believe in the company.

Here’s a great resource if you’re interested in stocks. NerdWallet offers an incredible team of writers and financial advisors that simplify the entire process of evaluating stocks and other financial products. It’s like they made the site for financially illiterate twenty-year old’s.

Pick an investment play in your twenties but stay clear of impulse buys and get-rich-quick schemes.

Do your homework, and I mean actually do your homework.

3. Put money into a side hustle

Side hustles are a hedge against career uncertainties.

This problem is, most people don’t work to get better at their side hustle.

Influential blogger and psychologist Tom Hardy once noted how writers (especially on Medium) fail because they don’t do the deliberate practice required for improvement. They don’t invest in skill development and end up writing 100 bland articles.

If you’re a fitness trainer, then pay a little to attend a workshop or get another designation. If you’re a social media manager, then pay for an online course about how to dominate TikTok or a course about copywriting on social media.

Build your list of qualifications and engage in the deliberate practice that will separate you from everyone else.

4. Start a newsletter

Substack is the best bet I’ve ever made.

People think a newsletter is solely about selling a product or providing information for subscription fees. Not anymore. It’s become something else entirely.

The best newsletters thrive off super fans. Their audience subscribes, not for the perceived value, but because they love the creator and will pay to see what comes next — a system like OnlyFans, except without the explicit content.

You will not be an overnight success. But that’s the beauty of it. Start by asking 30 of your friends to join your newsletter, then post at least once per week. Talk about whatever you want: what you’re working on, thoughts on a recent event, hacks that you’ve learned, any message you want the world to know.

Starting with a small audience is a magical thing. As noted by entrepreneur Paul Jarvis in his book Company of One: “starting out small and without a massive audience is perfect because it enables you to gain experience and play with your business ideas. Not to mention that there aren’t many people watching if you fall on your face.”

Keep at your newsletter for six months, one year, three years, who knows what might happen!

5. Invest in a mindfulness practice

No more eye-rolling. A calm mind is the key to longevity.

Marc Benioff, the CEO at Salesforce, has installed mediation rooms throughout the Salesforce Tower in San Francisco, and Google installed “light-filled antechambers” in their office buildings.

I don’t blame them. Millennials are constantly darting attention between career goals, cool life experiences, and, lest I forget, finding a life partner.

We need to learn how to SLOW DOWN.

“Meditation can be a real conduit for self-awareness and a cure during stressful moments,” Says Yael Shy, a mediation expert and the author of the book “What Now? Meditation for Your Twenties and Beyond. “You can learn how to really love yourself. And learning to love yourself isn’t something that’s always taught.”

I’ve found that a regular mindfulness practice improves endurance — it’s a science-backed way to deescalate anxiety from burnout.

Life’s a marathon, so do what you can to improve your endurance.

Take a bet on mindfulness.

Put your cards on the table

Treat your twenties like Chris Rock at a dive bar and place little bets on opportunities that may never work out.

What you learn along the way will accelerate the success of your next venture like you wouldn’t believe.

The better question is, how can you afford not to take the bet?