The $45K Wake-Up Call That Changed My Career

I Just Turned 33. Career Advice I Wish I Knew In My 20's.

Welcome to issue #9 of Side Hustle Stories. Each week, I share honest lessons from building a creator-led business while balancing a FT job and family life. No fluff. Just stories, frameworks, and behind-the-scenes decisions from someone doing the work in real-time. If you're building your own thing on the side—or want to—you'll feel right at home here.

Ten years ago, I thought I'd made it.

Fresh out of Stanford, I landed my dream job at the NBA. I was going to be the next Asian commissioner. Or at least a CEO. The vertical challenge of being 5'7" meant playing professionally was out, but leading the organization? That was the dream.

Then I saw my first annual salary: $45,000.

In New York City. Where a sad desk salad costs $18.

But the money wasn't even the worst part. I was drowning in bureaucracy, office politics, and the soul-crushing realization that my "dream job" was actually a nightmare. Every cocktail party, someone would gush: "Oh my gosh, you work at the NBA!" Meanwhile, I was calculating if I could afford both rent and groceries that month.

So I did what every panicked twenty-something does: I applied to business school. All of them. Harvard, Stanford, Wharton, MIT, Chicago, Columbia—my desperation had no limits.

The results? A masterclass in rejection. Some schools just said no. Others waitlisted me first, then said no. It was like getting dumped in slow motion, seven times.

The Sunday Morning That Changed Everything

Two and a half years into my NBA career, I hit rock bottom. No business school lifeline. No better job prospects. Just me, spam-applying to hundreds of companies like a human resume cannon.

Then my uncle called.

"Preston, grab a piece of paper. Draw a line down the middle."

I thought he'd lost it. But I was desperate enough to try anything.

"Top left, write 'What.' Top right, write 'Why.' Now list five things you want in your next role and why you want them. One sentence each. Keep it crisp."

That simple exercise became my career GPS. Here's what I wrote:

1. What: Make more data-driven decisions
   Why: I'm tired of throwing spaghetti at walls and hoping something sticks

2. What: Be more creative in my role
   Why: Creating new ideas and pitching them to clients energizes me

The clarity was instant. I didn't want to be a data analyst. I wanted to be in marketing—where data meets creativity. Where insights drive business.

Suddenly, I wasn't desperately networking with everyone. I was having strategic conversations with specific people. Including my old ESPN supervisor, who happened to be the SVP of Marketing at CBS Interactive.

One lunch later, I had a new job that actually aligned with what I wanted.

The Communication Shift Nobody Teaches

My mentor at CBS dropped another truth bomb: "It's not about what you do. It's about how you communicate what you do."

I'd been vomiting tasks at people: "I manage collaboration tools, build dashboards, coordinate projects..."

Boring. Forgettable. Career-limiting.

So I developed the PCSB framework:

• Problem

• Cause

• Solution

• Benefit

Here's the difference. One of my ISA students used to explain his company like this: "We connect businesses with customers by leveraging data to find targeted prospects..."

Snooze.

After PCSB: "Businesses are drowning in customer data but starving for insights. That's because they collect information without a strategy for action. We build systems that identify your highest-value prospects and automate outreach. Result? Our clients see 3x higher conversions and cut acquisition costs in half."

Same company. Completely different impact.

The 730-Day Experiment

Fast forward to August 2022. I'm 30, working at Lucid Software, and feeling that familiar itch to build something bigger.

So I flipped my Instagram from private to public, grabbed my phone, and recorded a terrible TikTok about networking. Two hours of work. 200 views (thanks, Mom).

But something clicked. I could teach communication skills to anyone, anywhere. So I made a crazy commitment: one video every day for two years.

Not because I had a master plan. But because I believed (and still believe) that your personal brand isn't a nice-to-have—it's an insurance policy. Your moat. Your distribution channel that nobody can take away.

Year one was brutal. 3,000 followers after several hundreds of videos. Then one video hit 3 million views, and everything changed. Today: 396K on TikTok, 283K on Instagram, hundreds of coaching clients, and multiple revenue streams.

All while leading BD at Lucid full-time.

Your Wake-Up Call

Here's what that $45K salary taught me: The pain of staying stuck hurts more than the pain of changing.

If you're in your 20s or 30s feeling like you're driving with a broken GPS, try this:

1. Do the What/Why exercise. Five things. One sentence each. Get ruthlessly clear on what you actually want. [Grab my template here—no sign-up required]

2. Learn PCSB. Stop listing tasks. Start telling stories. Practice explaining your work to someone unfamiliar with it using Problem-Cause-Solution-Benefit.

3. Build in public. Your personal brand is your career insurance. Pick your medium—video, writing, speaking—and start. Consistently. Even when no one's watching.

The best time to start was yesterday. The second best time is today.

What's your wake-up call going to be?

-Preston

P.S. If you're ready to level up your communication skills and stop rambling in high-stakes moments, check out The Impromptu Speakers Academy. We'll turn you into someone who speaks clearly and confidently on the spot—no scripts required.