The 5 Uncomfortable Questions You Need to Ask Yourself in Your 20s to Win in Life

I spoke on an alumni panel recently at my alma mater. Every time I step back on campus, I’m reminded of how far I’ve come since 20—but I also realize, 20-year-olds haven’t changed.

It’s been seven years since I was a student, yet one thing remains the same regardless of how much change has happened in the world: young adults are still wandering, uncertain about their future.

If this is you—feeling anxious and uncertain about the road that lies ahead. Please know that you are seen and heard. I was you not too long ago.

The uncertainty and anxiety are not a lack of knowledge though. All of these students are brilliant—fluent in AI, data analytics, and digital marketing, to name a few. But they all shared one common blind spot: they haven’t asked themselves the hard questions about who they are and what actually matters to them.

One student pitched me on a marketing internship. When I asked why she wanted to work at our company, she said, “I don’t have healthcare experience yet, and my family is full of doctors. Since I’m not becoming a doctor, I figured this was a way to ‘pay back into the system.’”

I felt for her. This was a terrible answer. She wasn’t chasing her dream—she was chasing someone else’s.

I see this happen all too often.

We fall into the trap of what we think others want for our lives, without considering why we would waste time living out a story that isn’t ours?

If you’re reading this and wondering whether you’re on the right path, living out your story, rather than someone else’s, here’s the truth: you should be asking yourself these 5 brutal, uncomfortable, and necessary questions right now. They’ll help you get clear on your direction, your purpose, and ultimately, lead you to a more prosperous life.

1. Am I actually learning, or just collecting certificates?

Degrees, certifications, and courses look nice on paper. But can you:

• Think Strategically?

• Write persuasively?

• Sell Something?

• Solve real problems for real people?

Skills > Credentials. Every time.

2. Am I choosing short-term pleasure over long-term greatness?

Another weekend wasted at the bar?
Another night bingeing Netflix?
Another hour of aimless scrolling?

Your choices are compound interest. The people you admire now sacrificed short-term pleasures to build long-term freedom and prosperity. The problem for most people is that you can’t see the sacrifice—trust me, it’s there.

3. If I lost my job today, how long could I survive?

Your paycheck is a fragile illusion of security. If you’re not saving, investing, or building skills that enable you to build income streams outside of your 9-5, you’re not setting yourself up for success.

• Ask yourself, how much cash do you have saved? (rainy day funds are still important)

• What skills can you monetize today if you needed to?

P.S. If you’re saying “I don’t have any skills” that’s probably not true. You just haven’t looked hard enough. If this makes you nervous, then create a fun challenge for yourself by embarking on a new experience and/or learning a new skill.

4. Who’s actually influencing my decisions?

Most people are unknowingly living out someone else’s script.
Their parents.
Their friends.
Society.

Look around.
Would you trade lives with the people you take advice from?

If not, why are you listening to them?

5. If I keep living like this, where will I be in 5 years?

The harsh reality:
Your habits today = Your life tomorrow.

If you’re:

• Avoiding strategic risk

• Making excuses

• Wasting time

Then in 5 years, you’ll be exactly where you are now.

But if you:

• Invest in yourself

• Build real skills

• Take uncomfortable action

Then your future self will thank you every single day.

Your 20s are a launchpad for the rest of your life.
Ask yourself the hard questions now, so you don’t wake up in a decade wishing you had started sooner.

With you in the Journey,

Rebecca

Game-Changing Products & Services

• RUKR: RUKR is on a mission to make rucking accessible to everyone. Use the code, “REBECCAS” for 10% off and become stronger with every step.

• The Creator MBA-A Business Playbook for the Modern Age: What if you started running your life like a business? Justin Welsh built a $5M+ one-person business without ads, a team, or complicated funnels. But here’s the secret: his frameworks don’t just apply to content creators. Whether you're a consultant, freelancer, coach, or entrepreneur, The Creator MBA teaches you how to:

  ✅ Understand your audience like a seasoned marketer
  ✅ Refine your offer so customers can’t say no
  ✅ Build leverage to your offer, service or product
  ✅ Convert prospects into paying clients with predictable systems

  This isn’t just a content strategy—it’s a blueprint for long-term independence. Whether you sell services, tangible products, digital products or your expertise, these principles will help you attract customers, monetize your skills, and scale efficiently. Treat your life like a business. Learn the system. Build your future

Exciting Community Initiatives

• From the Farm: Shake the Hand that Feeds You! Get connected with your local, family-owned farm, ranch or homestead, creating a secure parallel economy that champions food sovereignty and resilient food supply chain.

People I Love Learning From

Share Your Story & Build Your Life on Beehiiv

Beehiiv powers the world’s top newsletters. By democratizing access to sharing stories, building companies and brands, Beehiiv provides everything you need to succeed on one single platform. Start sharing your story today, for free, on Beehiiv.