What I wish I knew about business in my 20s

If I could write a letter to myself, this is what I would say.

A lifetime in the private sector has taught me innumerable lessons, both fun and painful, personal and professional. None of these things I could have been taught in school, or through an online course, or a how-to book. These are lessons I had to learn, and apply, myself.

You may understand the importance of these lessons, you may hear about them every day, but until you actually LEARN them, your potential success will forever be limited, and your growth slowed. Not to mention the path to success will be all the more difficult without these tools.

While my experience has been mainly focused on the financial, management, and private equity side of business, these lessons can be found in every autobiography from artists and designers, to lawyers and investors.

These are the four lessons I wish I could go back and hammer into my 20-year-old self.


In my 20s, I was always in too much of a hurry. In a hurry to complete my degree, in a hurry to get that next job, in a hurry to take that next step.

It all worked out well in the end, but in some regard, I paid a slightly too high price in the other areas of my life. I did not enjoy where I was at in the moment, at least not as much as I should have.

The reality is, notwithstanding my eagerness and impatience, I would have reached the same level of success, probably even quicker, had I just been a little more diligent and focused on where I was at the moment.

Racecars finish the race faster when they take a few seconds to change out their tires, instead of going 100% the whole race.

Now that I am a little older, I’m more aware of all the time I spent focusing on things that were out of my control, and that is one of my more significant regrets.

I would tell myself to focus on the present, and enjoy it because it goes by fast. Certainly don’t lose sight of your goals, or the hunger that drives you towards them. But temperate it with a degree of patience so that you can extract the maximum value out of your time, and more importantly, so that you enjoy it to the fullest extent.

Be more disciplined with the company you keep

Johann Wolfgang von Goethe said, “Tell me with whom thou art found, and I will tell thee who thou art.”

If you’re a good person, then you can have a good time with just about anybody. The ability to get along with everyone, and find the best in friends and enemies is an admirable trait. But those with whom you choose to associate yourself does, and will, have repercussions for good or ill.

Hang around the hoop with quality people, so that you can absorb their attributes and attitudes. Their knowledge and support will play a monumental role in your growth. You’ll often hear that you are the product of the 5 people you spend the most time with, and I think that is the absolute truth.

In the same light, I would say be diligent in removing those who are negative influences in your life, those who may bring you down, who aren’t supportive or bringing any value to your life.

I was not as focused on this aspect early on and so it took me a few years, a decade even, to really clarify my thinking and my skill set. By trimming the fat, so to speak, I could have saved myself a lot of headache and wasted energy.

Practice Discipline

My definition of discipline is, “doing what you know you need to do, even when you don’t feel like doing it.”

The challenge with entrepreneurship or the creative process is that there is always temptation to just do the fun thing, or do the task that looks like it should be next. Simply put, to chase after the “shiny object”. My advice to myself would be: don’t!

Stay disciplined in what you do, how you do it, when you do it, whom you do it with and even if you do it at all. If you stay focused on the mission, the objective, the strategy, the tactics and doing what needs to be done, it will only enhance your likelihood of success.

Yes, there are other issues that can add to your success and other necessary skill sets that are necessary to succeed, but discipline is the primary skill that should always be on everyone’s list.


Naturally, of course, the real difficulty would be getting my 20-year-old self to listen. But if I could do so, I think it would’ve made things a lot easier along the way.

How many problems could have been solved if I only listened more carefully? If I took an extra few seconds to listen before responding? I would wager that I would have learned the lessons above faster, and at the same time avoided headaches and situations caused by poor communication, and lack of information.

Publilius Syrus said, “I often regret that I have spoken; never that I have been silent.”

This is where we can see it all pull together: patience, discipline, company, listening. If we take the time to plan out our day, week, month, and listen to the right company, we will see the barriers on our success melt away. The obstructions to our happiness, whether self-inflicted or imposed by others, will fade into meaninglessness. And maybe one day, we won’t have to write letters to our 20-year-old selves anymore.

Aaron Webber is a serial entrepreneur and CEO of Webber Investments LLC, as well as a Managing Partner at Madison Wall Agencies.

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