Advice To My 20 Year Old Self

My birthday was last week.

It got me thinking…

What advice would I give my 20 year old self?

I’ll admit that I was inspired by listening to this question asked by Tim Ferriss on his podcast. The question always yields some interesting answers.

Looking back on the past and saying “I wish I did…” is mostly counterproductive as there is nothing you can do to change the past. However, it can be useful for reflection and thinking about your future if managed properly.

Dear 20 year old Brian, here is my top three pieces of advice to you:


Develop good money management habits

Money habits will set the foundation for, and can determine, the rest of your life. Make them good habits. It wasn’t until I was 30 that I really started focusing on money management and that it stuck as a habit. Starting now will make it easier for you in the future.

This breaks down into three areas for me (in order):

  1. Create and stick to a budget.
  2. Eliminate, or minimize, consumer debt.
  3. Grow the “gap”.

Budgeting gives you the data of what your income vs expenses. Without that data, it is almost impossible to be good at money management. Creating and sticking to a budget is 1/3rd about the tool used to track spending, 1/3rd about the “why” behind budgeting, and 1/3rd about building the habit. I failed at the “why” and the habit in my 20’s, which caused me to attempt budgeting and give up. When I reached 30 I had found a better tool, YNAB, discovered my “why”, and stuck with the habit even when it was difficult.

Consumer debt should be avoided in almost all cases. The only exception might be student loans (which luckily I did not have) or a mortgage, and in those two situations minimize it as much as possible. Consumer debt is an anchor on your life.

Twice in my twenties I built up credit card debt because of spending more than I was earning (both times I dug myself out of it). I had a used car loan. I had a mortgage on a condo. Debt creates stress. It will limit your opportunities. So, eliminate the debt you have and think hard about if there are possible alternatives to taking on debt. Think about long term financial goals when making purchase decisions.

Grow the “gap”. A lot of money management advice is either “save more” or “earn more”. My advice? Do both. Minimize expenses first to get your burn rate low and then focus on earning more. The thing that matters most is that gap between what you spend and what you earn. Grow that gap as much as possible.


Be proactive in your career because it doesn’t build itself

You are the CEO of your career. Explore opportunities even when you don’t need to. Relationships are very important, focus on them. Be proactive. Invest in yourself. Stay curious.

Spend 10% of your time on your career – no one else will. Keep a pulse on the job market and find out what opportunities are out there. Talk to people. Start a side project or take a course to learn a new skill. Never stop learning or being curious. Be observant and view problems as opportunities. Find ways to solve those problems.

As an introvert, it will be a struggle to keep in touch with former co-workers, friends and clients. Figure out a system that works for you and leverage electronic communication to keep in touch. Go to events and keep in touch with people you meet. Loose connections can be the most valuable for your career. Spend the time building and maintaining relationships.

When you are becoming too comfortable it means you aren’t being challenged enough. The old paradigm of School → Work → Retirement is outdated. Don’t be afraid to start something new and fail at it.


Stop worrying so much about what other people think

Speak up more often and make your opinions heard. Don’t be afraid of an argument. Take a position. Put yourself out there.

Over and over again in my life I have spent too much time worrying about what others think of me, wondering if what I said was taken out of context, or how my position on any topic changes their opinion of who I am. As a result it’s caused me to stay quiet more often than I should have.

Worrying about what others think will only prevent you from living your life and being yourself. It’s good to have self awareness, awareness of the feelings of those close to you, and compassion towards others but that shouldn’t change your convictions. Take constructive feedback when it’s warranted – use that to aid your self improvement. Put yourself out there.

Making your opinions heard and taking a position on a topic shows that you care. That you have ideas. That you aren’t afraid to debate that point. Debating used to feel like arguing to me – something I avoided because it felt like there was no end game. Then I learned how healthy it actually is. Seek it.

Oh and one last thing – ask for help when you need it. There is nothing wrong with asking dumb questions and no reason to feel embarrassed for not knowing the answer. It will help you grow.



This list could be a lot longer but I wanted to keep it focused on just the top three. So I want to ask you…

What advice would you give your younger self?


PS I highly recommend reading The days are long but the decades are short by Sam Altman.