Avoid These 10 Painful Regrets in Your 20s

1. Not spending more time doing things I loved.

I wish I had spent more time doing things I loved and got me excited, like going to dance conferences, attending toastmasters, travelling the world, and exploring new places.

At the time, it felt irresponsible to focus so much on hobbies and enjoyment. I felt I had to always be thinking about my career.

Later, I realized that our 20s is the best time to learn who we are, what we like and dislike, and what our natural strengths are.

As life gets busier and commitments grow, it is easy to lose sight of the things that bring us joy, energy, and excitement. It is easy to lose sight of why we do what we do. It is far too easy to get stuck working hard for a job or life we don’t want.

Go into a self-discovery journey when there are fewer commitments in the way of your desires. Once you have kids, employees, mortgages, a house, loans to pay, and other commitments, it becomes hard to realize what you genuinely like and want. Become self-aware by experimenting with things you love.

2. Not pursuing my bucket list.

I had a huge bucket list of things I wanted to do like mentoring, and inspiring young STEM and female professionals, publishing a book, developing a patent, launching a youth conference about the future of education, and traveling the world.

I ignored my profound desires for a decade. In my mid 30s a sudden deep urge came to start over and to focus on my bucket list. It is a lot harder now.

I felt I had to stay focused to succeed in my career and that those bucket list initiatives were not going to support my traditional career path. I was too analytical about it. I suppressed my desires.

In my 30s, I learned that delaying my bucket list wasn’t going to make it easier and wasn’t going to erase the desire either. The opportunity cost of a certain level of success that you already managed to reach,  family, and financial commitments makes it a lot harder to find the time and courage to invest in our bucket list.

In our 20s we forget we have 4 or more decades ahead of us. We think we must get it perfect right from the moment we graduate. We define ourselves by the job title, company reputation, and the pay we get. And we forget everything else. Don’t ignore the other desires your soul points you towards. Allow yourself to explore them.

3. Not expressing myself more.

I wish I had expressed myself more at work, with friends, and in networking events. Because I didn’t express myself, I often felt bored in conversations and meetings, not understood, and not valued by coworkers and friends.  

In my 20s, I felt like I never had something important enough to say. I also thought everyone had better stories, ideas, and perspectives to share. Until I learned that people would paint the most uninteresting stories as blockbusters, and that many of my experiences were unique and sharable.

In meetings, I thought I should only speak if I was 100% certain of the relevance and accuracy of what I had to say. Until I learned that even very senior people confidently shared bad ideas and inaccurate facts all the time.

With friends, I didn’t want to be rude or be perceived as the know it all by sharing any amazing experience or positive stories. I felt I had to be humble and a good listener. Until I learned that people share their personal highlights most of the time and it makes them seem interesting.

In retrospect, I realized how important it was to express myself freely and boldly. The moment I finally decided to express myself, I found a wonderful husband, I got a promotion, and I found my dream job.

Don’t hold back from expressing yourself. Express yourself fully while still being respectful, kind, and considerate.

4. Not questioning others more.

When I consulted financial advisors, I believed they had my best interest in mind. I didn’t ask them too many questions. I was afraid of hurting their feelings by asking direct questions about their commissions, hidden fees, and own investment allocations and returns. 

When they had unclear answers, I felt uncomfortable insisting to have a clear explanation. Later, I realized they were going to make big profits out of my naïve shyness. They tried to exploit and manipulate me.

I also wish I had realized higher ups don’t always have the answers and have many flaws. I didn’t question them because I thought disagreeing was disrespecting authority.

Don’t feel any guilt questioning others in any way, even authority figures. Make your decisions with a proper understanding of their implications.

5. Not prioritizing myself.

I wish I put myself first in many occasions. I felt so loyal to my boss and my company that I had shingles and didn’t take a single day off. I skipped dental appointments to not be absent from work for even an hour. And I’d be so emotionally exhausted from work that I had no energy to invest in my health, personal finances, or passion projects.

I felt that the priority of other people was my priority. I felt I had to be loyal to them. Eventually they were all gone from my life. I realized how little benefit there really was in sacrificing what really mattered to me.

Be more intentional about your choices and where you want to spend your time and energy.

6. Not asking for what I wanted.

At work I wanted to attend industry conferences, do more leadership trainings, and participate in more strategic meetings. For many years I never asked or explicitly told my boss that I was interested in those things. Then, I’d be secretly frustrated because I missed out on many development and networking opportunities.

I didn’t feel entitled to ask and I certainly didn’t want to be judged as unreasonable. I felt anxious with what seemed to be a hard conversation. I felt like I had to deliver absolute incredible value (which I never felt I did due to impostor syndrome) before I could ask my boss for anything.

Later in life I saw people asking for what they wanted without giving anything more in return, and still getting what they wanted. My employees did this all the time and I didn’t find it unreasonable. There is a time to give. But you don’t need to give and receive from the same people.

Don’t feel guilty to ask for what you want. Don’t feel like you need to prove yourself before you ask. Don’t feel like you need to be generous before you ask for what you want.

7. Not staying in touch with my network.

I wish I stayed connected with my network. During much of my 20s, I ignored most of the people I met at college, in my earlier jobs, during networking events, and in my MBA program.

It wasn’t lack of interest in others. It was fear of social comparison, shame, and guilt for not staying in touch before.

Your networks will be your friends, get you jobs, and help you with your dreams. They also allow you to add value to others. I didn’t consider that they too had not stayed in touch with me. I had not realized that everyone had struggles. I had not yet learned the power of authenticity and vulnerability to connect with people.

Stay connected to people you meet along your journey. Your goal is not to be better than them, but to connect.

8. Not advocating for myself.

When I was 22, I really wanted to experience one night in an ice hotel. It was in my bucket list. I was lucky to find an amazing promotion to have that experience in Canada, so a close friend and I booked it. I waited for the perfect moment to inform my boss and ask for a day off to go to the ice hotel. 

My boss said ‘no’ and didn’t give me a good reason. I didn’t ask why and or challenge him. My friend went to the ice hotel and I lost that booking and the opportunity.

I was too afraid to challenge or negotiate a solution with my boss. I was upset with him and assumed he denied my request intentionally and for no reason other than to prove his power. Making assumptions and not standing up for my interests didn’t serve me in any way.

When we don’t learn the tools to defend our interests in a respectful way, and how to communicate our needs effectively, then we miss out and create resentment.

For you, that lost opportunity might be a job, a promotion, or a role in a project. Don’t wait for others to advocate for you. Advocate for yourself.

9. Trying too hard to be liked.

I wish I had focused on earning respect rather than being liked. 

My focus on likability made me a people-pleaser and less authentic. I did what I thought others wanted me to do. The fear of hurting people’s feelings paralyzed me.

As a woman, it is even harder to allow others dislike you and to demand respect. Over time, there is a significant career impact of focusing too much on likability. 

Let go of the need to be liked in your 20s, and you will gain so much freedom to choose the best path for yourself.

10. Measuring my value in time commitment.

I wish I had learned that my value is not in the hours I commit to something. For too long I showed my commitment to an employer, task, or friendship in the hours I dedicated to it. Because I associated my value to time spent doing things, I’d work long days unnecessarily.

Part of the problem was that I did not know how to communicate my value to others. I believed my time effort would speak for itself. But then people would use that belief to control my behavior and keep me working long hours.

The other problem was low confidence in my deliverables. I always thought my deliverables were not good enough (because of impostor syndrome).

Learn that your value is not in your time commitment and not even in your deliverables. You are a lot more than that.