Top 10 Things I Wish I Knew in My 20s

After thinking about my life over the past number of years, there are a ton of things I wish I knew earlier that would have put me well ahead of others in terms of my career and personal development. You learn a lot through your own experience, but why struggle in your 20s when you can look to those older than you?

You may agree or disagree with any of the points below, but these are the top ten things I wish I knew in my 20s.

1. It takes just one coworker to ruin your reputation

My first job out of college was in investment banking where I stayed for three years. I spent my first two years developing a reputation of being hard working, having a great attitude and a good ability to work independently. Fortunately, after my second year I was ranked top bucket amongst my analyst class and had developed a good reputation.

My third year turned out to be different. I switched groups to work in a new industry and had to redevelop my reputation since I worked with a whole new set of coworkers. My first six months I used the same playbook that I did to develop a good reputation my first two years.

Everything was going smoothly until I realized I did not want to stay longer-term and had to focus hard on getting a job on the buyside. There was this new associate straight out of MBA that I was assigned to work with on a pitch. He took everything so seriously as he did not realize yet what was important and what was not.

I ended up not putting in as much effort working with him and dropped the ball on a few tasks as I wanted to interview and find my next job.

Little did I know that my performance on just one assignment with that associate would be the reason why I did not get top-bucket my third year. Additionally, I later found out that others in the group started thinking less of me due to what this associate said.

Lesson Learned: Do not become complacent and think everyone will always think highly of you. All it takes is poor performance with one person to ruin your reputation, so give 100% effort with everyone that you work for. 

2. Making money is not all that cracked up to be

I’m not sure about you, but for me making six figures right out of college was a dream come true. I grew up in a middle-class lifestyle and was not exposed to the different levels of wealth that you see in NYC. I made a $70K base salary and my first bonus after my one year was $55K. That bonus payment alone was more than the average American makes in a year.

For the first few years I was ecstatic when the bonus payments hit the bank. I started to learn how to invest it and it was somewhat of a fun game. However, then reality kicks in and you start to question why you are working so hard and making money when you have no time to spend it.

The bonuses turned into just numbers in your bank account that keep going up. You begin to realize that in order to be considered wealthy, you need to make significantly more to experience a change in your lifestyle.

I am in no way saying that making money is a bad thing. You just start to become numb to the amount that you are making and realize that you still have the same problems as you had when you weren’t making as much (ie. figuring out what you want to do with your life, having free time). Additionally, your expectations increase as you start to compare yourself to others who make signficantly more than you.

Lesson Learned: Making money is great, but do not expect it to make you happy or solve all of your problems.

3. Going out past midnight drinking accomplishes nothing

When you were in college, you had so much free time and no real responsibilities. That all changes when you start working full-time, especially if you landed a job in investing banking.

During my first few years out of college, I continued to go out every Friday and Saturday night. My friends and I would work extremely hard during the week and blow off steam on the weekends. We showed up hungover to work on Saturday/Sunday if we had to come in the office.

Now this was okay for the first couple of years since as an analyst you do not have any major responsibilities and usually have an associate check over all your work. Once you transition to the buyside at a private equity firm or a hedge fund, you no longer have anyone checking your work. On top of that, you have a ton more responsibility and autonomy. Any analysis that you do can have a direct impact on if your firm invests millions of dollars into a company. So, if you make a mistake then you are personally responsible.

You can not afford to be hungover at work when you are in these buyside roles. You need to be able to think, read and process a ton of information. It is different in banking because there are real monetary consequences to the decisions that you and your team make.

The most common misconception that most people have is that you work less on the buyside. While at times this may be true, in general it is a complete lie. You will have less down time and are more focused during the day to get your work done.

Lesson Learned: Once you get older, your body cannot handle the inconsistent sleep schedules and drinking habits of your younger college self. Once you realize that it takes longer to recover and the only free time that you have is on some Saturdays and Sundays, then you want to maximize that time as much as possible. Being hungover and staying in bed is just not worth it anymore.

4. Grass is always greener

I am talking specifically about your current job and the job you think you want that is better (although this concept applies to relationships as well, but I am not here to give you relationship advice).

For example, virtually everyone who is an investment banking analyst believes the buyside is the promise land. They think you work less, make more money and live a better life in general. This is a complete lie and it is not healthy to go in to your new role with these expectations.

When I transitioned to the buyside at a multi-manager hedge fund, I was absolutely excited and could not wait to start. I thought the work would be way more interesting and overall a better role for me longer-term. Little did I know in just one year I would quit that very same role because I knew it was not for me. I realized that there were aspects to my old job in banking that I really liked that were missing in my new role.

Everyone is naïve when they are young and usually follows the herd mentality. I wish I talked to more people who were already in the very same roles that I thought I wanted. This would have allowed me to get a holistic view of both the positives and the negatives of different career paths.

Lesson Learned: Your dream job may turn out to be completely different than you were expecting. Make sure to do all the research you can rather than listen to the herd.

5. You are what you say you are and you will become who you say you will become

I know… this may sound a little cliché, but it is completely true. Your everyday thoughts about yourself, your job, your career, etc. end up becoming true. You may think this is complete bogus, but the way you think influences many different aspects of your life.

I’ll provide a few personal examples. In college I was not considered one of the smartest in my class. I was fortunate to go to a good undergrad business school and landed a number of investment banking interviews. I knew in my mind that this was exactly what I wanted to do and I focused all my energy on landing a job in the industry. My dreams became true and I started my career in investment banking

A negative example… Once I transitioned to the buyside at a multi-manager hedge fund, I quickly realized that it was not for me. I kept complaining to myself why I even considered this job. Kept saying I hate it, I want to quit, I want to quit, etc. And in just one year, I was experiencing signs of burnout and quit the job.

Who knows.. if I had more of a positive attitude, maybe I would have been able to succeed in the new role.

Lesson Learned: Always keep a positive attitude in life, even when something turns out to be completely different than you expected. Your negative thoughts influence your behavior and have a direct impact on what happens in your life.

6. Social media is pointless

Remember having a lot more free time when you were a kid through high school? You had so much more time when you woke up, during the day and when you went to bed. Nowadays, everyone is on social media and constantly checks their iPhone for any new updates from their friends.

Once you get older you start to value your time a lot more. I guarantee you that you can easily find an extra two hours a day (at least) if you stop using social media. Use that time to go to the gym, start a side hustle, read a book, catch up with old friends, or anything else that is productive!

Lesson Learned: The older you get the more you realize that social media is a complete waste of time.

7. Speak up when you have valuable insights / opinions

I will admit, I was intimidated once I started my first job out of college. All of my coworkers in investment banking, especially the higher ups, were extremely successful and made so much more money than I thought was possible growing up.

It took me a while to get accustomed to this new environment. Even though I worked hard and had a good reputation, I was consistently told to speak up and provide my own opinions. I learned over time that once you gain the respect of others, they look to you to contribute to the conversation.

Now there is a big difference between speaking up when you have something valuable to share versus speaking up just to get your voice heard. I have come across a ton of people who say the most ridiculous things in front of their bosses or clients just so that they can say they said something. Don’t waste people’s time if you have nothing important to say.  

Lesson Learned: Don’t be shy and speak up when you have some valuable information to share. On the other hand, don’t annoy people if you have nothing important / insightful to share.

8. Relationships are a two-way street

I know I said I am not here to give relationship advice, but think this point is very important. You learn a lot after your first serious relationship ends. It is just like experiencing failure in any other parts of your life. You learn what works, what doesn’t, etc.

Being able to communicate is the number one lesson I learned. If something bothers you, you should bring it up and talk about it. Do not keep anything to yourself as it will grow inside and cause you to resent your significant other, which will lead to other problems.

Additionally, do not criticize your significant other if she brings up something that bothers him or her. You need to be able to put yourself in their shoes and try to understand whatever it is that is bothering them.    

Lesson Learned: At the end of the day, to continue having a healthy relationship you must be able to communicate and listen properly.

9. Must work towards diversifying your income cause a career is risky

For some reason it is a universal accepted belief that having one stable job is the least risky way to make a living. Work at the same company 9 to 5 to pay all the living expenses for you and your family. Stay there for a long time, build a reputation and the chance of you ever getting laid off is zilch.

Hate to break it to you, but having one source of income is the riskiest way to live your life. At the end of the day, the company that you work for is a business that cares solely about profits. If they can cut costs through automation or replace you with someone who costs less, then they most definitely will.

You must learn to find a way to diversify your income in your 20s so you are not so dependent on your full-time job. This is the best path to financial independence.

Lesson Learned: It is never smart to put all your eggs in one basket. Start a side hustle to diversify your income stream.

10. You are the average of the five people you hang out with most

Choose your close friends wisely because who you hang out with has a direct impact on you.

In college I would primarily hang out with the guys who were in my fraternity. Naturally I ended up going out with them all the time. Drank a lot, gained some weight and was absolutely not productive during my senior year.

Nowadays, I am way more selective in who I hang out with because I know their behavior/personality rubs off on me. I have now turned into a morning person because one of my old roommates used to wake up early as well. He would also go to the gym everyday, which I have now adopted into my usual routine. 

If you surround yourself with unambitious people, you yourself will likely be unambitious as well.

Lesson learned: Figure out what type of person you want to become and surround yourself with people who have those exact same qualities.

If you want to read more about life advice from very successul people, be sure to read Top Life Lessons from The Ride of a Lifetime (Bob Iger).