9 Big Regrets of a 31-Year-Old Woman

#1 and #7 could have been life-changing

Photo by Marcos Paulo Prado on Unsplash

I have to admit, my 30-something life is pretty great.

A lot of the regrets, or mistakes I’ve made shaped me into the woman I am today.

However, this is not to say that there aren’t things I didn’t want to change in my 20s.

And I have a few big ones.

1. Giving too much f*ck about what people think

“You want praise from people who kick themselves every fifteen minutes, the approval of people who despise themselves.” — Marcus Aurelius

I once thought it was fear - fear of judgement and social banishment. This is partly true. The other part is arrogance. I had all these ideas in my head, and all these things I wanted to do, but I did nothing. Why?

Because I was arrogant. I believed the world was watching me, talking about and laughing at me behind my back.

It’s not.

The truth is, people don’t think about me, period. Because they don’t know who the f*ck I am.

At 31, I still care about people’s opinions of me, but far less than before.

We all do it. The less we obsess over it, the freer we become. That’s the thing about freedom — it comes from what we choose not to do. When you decide to stop caring so much, you unlock the ability to pursue what truly matters to you.

2. Thinking too much and doing too little

“You can’t build a reputation on what you are going to do.” – Henry Ford

I had so many dreams:

Write a New York Times bestseller, create a website that generates $1000 monthly, build an app that attracts 100K users on day one, and makes me millions in three months.

Cute.

Those ideas kept my blood boiling and heart racing at 3 o’clock in the morning. I pictured my bright future, lying on a beach in Cancun, holding a margarita with my right hand while being fed grapes from my left.

Photo by David Vives on Unsplash

And then, there is no “and”.

Because I did absolutely nothing.

I kept waiting. Waiting for more free time, for a sudden burst of genius, for the perfect qualifications.

I never became fully “qualified”. Because I never took a single step.

3. Not leaving my exes sooner

“Sometimes, you have to forget what you feel and remember what you deserve.” — Unknown

My exes were great people, but they weren't right for me. They weren't right for the Mandy I was, at that moment in time.

I was clinging to a false sense of security, scared that if I let go, I would never find happiness.

But now, in my thirties, I’m happier than ever.

If you’re brave enough to say goodbye, life will reward you with a new hello.

4. Basing a major decision on a boyfriend

“You have to do what is right for yourself. No one else is walking in your shoes.” — Unknown

Nine years ago, my boyfriend at the time decided to enroll in a one-year Commerce Masters program. Believing he was “the one,” I enrolled too, just to stay close.

In the grand scheme of things, I’ve done fine.

I’ve landed great consulting and data science roles, living and working in vibrant cities like New York, Beijing, and London. I’ve met fascinating people, enjoyed fun dates, and made lifelong friends. 

But sometimes, I wonder.

What if I had chosen a Computer Science or Machine Learning program in California instead? Would I have more opportunities as an immigrant on a skilled worker visa?Would I have more freedom in choosing where to live? Would I cross paths with people in Silicon Valley who’d inspire me, challenge me, and mentor me?

Maybe I’d have built my dream life faster.

But I’ll never know. And life moves forward, never backward.

5. Not investing sooner

“Time in the market beats timing the market.” — Kenneth Fisher

I despised easy money.

I despised easy money like a 20-year-old Asian immigrant who's told that hard work and academic excellence are the only yardsticks of success.

Isn’t it cheating to use money to make money? Hard-earned cash came from hard work, right?

I was busting my ass working 50-hour weeks in consulting, splurging on over-priced Manhattan cocktails, while my modest savings sat idle in a Bank of America current account, earning nothing.

Oh, the folly of youth.

In a previous story, 3 Big Investing Mistakes, I emphasized that waiting for the "right" moment or waiting for more disposable income is not the way to go.

If I had invested $1,000 in the S&P500 a decade ago, it would have grown to $3,277 today.

Photo by micheile henderson on Unsplash

The way to go is to start.

6. Neglecting soft skills

“You can have all the hard skills in the world, but without soft skills, you will not get far. Communication, empathy, and understanding are critical.” — Warren Buffet

Hard skills get you walking. Soft skills get you sprinting.

I used to roll my eyes when alumni career panels hyped “communication” as crucial. Doesn’t everyone communicate daily? What’s there to master?

I couldn’t have been more wrong.

Early in my career, I prided myself on my technical skills. I loved coding more than connecting with people or building relationships.

Later, I realized communication and storytelling are vital in data science. Without them, your insights never reach decision-makers.

I also regret not sharpening my strategic thinking. I didn’t read enough books or follow thought leaders. Now, as I build my own business, I’m learning the ropes of branding, marketing, and sales. But I could’ve accelerated my growth if I’d focused on these areas earlier.

7. Not starting a side hustle sooner

“Do something today that your future self will thank you for.” — Sean Patrick Flanery

Side hustles stack the odds in your favor. Multiple streams of income protect you from the world’s whims.

I let my day job consume me. I was too risk-adverse to do something new, too naive in believing the world would stay the way it is.

When I left the corporate grind to build my own projects, I had nothing to build upon—no established projects, no network to leverage.

8. Not lifting people up enough

“People will forget what you said, people will forget what you did, but people will never forget how you made them feel.” — Maya Angelou

Have you ever met someone who radiates confidence, listens intently, and genuinely encourages you?

That wasn’t me in my early 20s.

I felt awkward complimenting others, thinking that uplifting someone else would somehow diminish me. I feared that giving compliments meant sacrificing my pride, and that showing admiration exposed my own inadequacies.

What I lacked was social intelligence—the empathy to make others feel valued rather than trying to showcase my own importance.

I am striving to become that person who cares, listens, and inspires.

9. Concealing weaknesses

“To share your weakness is to make yourself vulnerable; to make yourself vulnerable is to show your strength.” — Criss Jami

I used to believe that “adults” had everything figured out, so I needed to act like I did too.

But the truth is: no one has all the answers. Everyone is just winging it as they go.

I discovered that exposing my weaknesses showcased my authenticity and built trust, which I detailed in 3 Painful Mistakes I Made as a Junior Data Scientist.

In a constantly changing world, it’s impossible to know everything. Authenticity now matters more than ever.

Imagine the freedom of admitting you don’t know something and people still respect you.

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I don’t dwell on the past too much or waste time on things I can’t change. Instead, I am documenting my regrets, so I can learn from my experiences to make the most of the next decade.

What about you? What’s on your list of regrets?