5 Lessons In 5 Years Since Graduating (A Letter To My Sister)



Yippee! You’ve graduated after four years of hard work, good times, and your first taste of freedom. I am so proud of the woman you have become; and I truly admire your ability to achieve academically while maintaining perpetual optimism and light-heartedness. You are an absolute pleasure to be around 🙂

If you recall, I wrote you a letter after your high school graduation which was a collection of advice I thought a college student may find helpful. What I thought would be fun is if I wrote down 5 lessons, with stories where possible, that may prove useful as you get ready for the real world. Then hammer away 21 unsolicited suggestions with no context. 

Lesson 1: Who you surround yourself with and your inputs are some of the most important decisions you can make.

As you know, when I graduated I moved to Richmond, Virginia for the summer and lived with 12 other young men as we went through the training program for our new jobs. As fate, or dumb luck, would have it I was surrounded by people who were way smarter than I was. I noticed almost immediately that my vocabulary was getting more robust on a daily basis, and I was thinking more critically before answering questions…I was even complaining less. What the hell? All from just hanging out with a group of people? Yes, it is called regression to the mean. We are tribal animals, so humans want to get on with other humans by being more like them. But here was the secret that I found: even if you cannot surround yourself with these characters on a daily basis you can control who you pick up the phone and call during your commutes. This also has a big impact on you. 

Speaking of picking up the phone….if you don’t want to consider deleting your social media like I have, I would recommend two things: 1) do an audit of everyone you follow that would show up on your feed, are they posting the type of content you want to absorb? 2) One practice I developed was deleting my Instagram after posting an image so I wasn’t checking who “liked” it every 10 minutes. I found myself spending way too much time looking back on seeing who double tapped my photo. Which, it turns out, is not a good use of time :).

Lesson 2: “Reinventing” yourself, it turns out, is really easy to do. All you need to do is get started and be consistent.

My first camping trip since I was a cub scout was when Spen, Porter and I went to Green Ridge State Forest. With very little research we packed our bags and hit the trail. Carrying with us loads of unnecessary stuff we marched 17 miles in what turned from a clear day to rain, to sleet, to snow. Oh, then we tried to squeeze the three of us into a two person tent. It was so cramped that Spen decided to sleep outside after a few hours of sleepless tossing and turning. It was a funny sight to see him covered in snow the next morning! But we made it, and we lived to tell and learn from the tale. The next time we went out we were more prepared, as with the time after that. Now 4 years have gone by and we feel like we’ve got our act together, and I can pack my bag in under an hour and be ready for a weekend in the woods. 

When I started Jiu-Jitsu two years ago I was terrible. My next 100 blog posts will probably be better than my first 100, and my first toast master’s speech was filled with “um’s” and “ah’s”. It turns out you are not a finished product. You are still highly malleable and where you spend your time will still shape the person you are.

Lesson 3: Use your 20’s to build a strong foundation by understanding compound interest.

Take a look at this:


This is assuming you start with $3K invested (maybe from graduation presents :)), and continue putting in $800 a month for 50 years compounded at 8%. The powerful thing to be aware of is how the lines separate so sharply after year 20. In fact, the difference between year 40 and year 50 is $3M!!!

Let’s get more concrete. What if you started with $0 and only invested your daily coffee money as you started getting a free cup from the office. What would that look like over this same time span? Assuming you get a $3 cup 7 days per week it would be over half a million dollars!!


Seeing the results with money is fun, exciting, and visual but the compound effect applies to many areas of life. If you start with reading one book a month, how much knowledge would you have in ten years? For whatever your goals are don’t underestimate the power of small steps and the daily effort. Consistency and persistence are superpowers. 

Lesson 4: Get comfortable being uncomfortable.

The first time I was turned down for a promotion was because I struggled with having the difficult conversation….because it’s hard! No one likes being a bad guy or gal! I thought: dang, well now you know this thing you don’t like doing is going to hold you back – so it’s time to get better at it. I keep a journal and I started reflecting on when I would shy away from having a difficult conversation or when I plowed ahead. I started to notice commonalities for when I would engage and when I backed down. In fact, I made a tracker in my journal for every time I backed down and as the days and weeks went by I became more and more comfortable. I even took a job where I would be answering the phone 50 times per day so I would get better at talking to angry people. 

Here is the real secret: comfort will betray you. You already work out a ton so you know that you feel better after you put in the work. I cannot wait for the first time we go camping together and you experience the delta of sleeping on the ground vs. your bed the next night. Keep your needs low, and do hard things. 

Lesson 5: Find your role model. 

We were both lucky to have older siblings; I cannot express how much I learned from watching our older brother, Brian. Maybe you feel the same way. After I moved out of the house I was surprised to find similar role models along every step of the journey: Porter in college, volunteers I met through SigEp, and many through work. 

The beautiful thing about the information age is that you can also have role models and mentors who you never actually meet. 

You wouldn’t believe how many hours of podcasts I have listened to from people I looked up to: people from business, fitness, martial arts, investing, and many places in between. There came a time when I was listening to Jocko Willink or Tim Ferriss and a guest would ask them a question and I would know what they would answer with before the words came out of their mouth. Finding a good role model is a great way to analyze situations: “what would so and so  do here”, and it also opens your mind to different paths in life that people take. It doesn’t matter if you disagree with 30% of what they say or even 50%. As Bruce Lee once said: “take what you need, discard what you don’t, combine to make something uniquely your own.” Find yourself a badass lady to model yourself after, but don’t be afraid to be your own person and add your own flavor 🙂 

21 Unsolicited Suggestions:

  1. Answer the phone and greet people with enthusiasm. More than you think is necessary. It’s fun and makes for a better interaction. 
  2. Time moves like the hour hand: you don’t realize how much it is moving in the moment, then you look up and much has passed. Don’t waste time. 
  3. Break a sweat once a day. 
  4. Choose muscle over motor transportation whenever possible (i.e. bike, take the stairs, or walk). Habits built around movement are important to establish now; you may not have an optimized exercise routine forever so this is good to fall back on. 
  5. Read at least one book a month. 
  6. Keep a journal. 
  7. Develop a meditation practice. 
  8. Keep expanding your cooking skills. It is a great creative activity, a good way to entertain, and saves you money. 
  9. Buy higher quality things by understanding the lifetime value of said things (cost per year).
  10. Give away one thing for each new thing that comes your way.
  11. Try to save 50% of your income.
  12. Understand that the big 3 expenditures for the average American is housing, transportation, and food. 
  13. Keep housing and transportation as low as possible and invest in your health with high-quality food. 
  14. Sleep 8 hours per night. 
  15. Quit social media.
  16. Avoid live television.
  17. Treat your travel like education and learn something from the different cultures you visit. 
  18. Understand that the first line of self-defense is awareness: avoid bad situations. The second line of self-defense is your feet: running. The third line of self-defense is preparedness: hand-to-hand combat. The first two are the most important. You would be well-served to learn some of the third. 
  19. Spend time in the sun and in nature, even if that is your local community park.
  20. The more often you are a stranger, the more comfortable you become being one. Join a club or group of people that you don’t know; be the first one to introduce themselves when walking into a new situation. 
  21. Understand that after high-school you have spent more than 93% of your in-person parent time with our parents. Each time you leave them, try to do so on a positive note. I recommend reading the tail end before holiday’s. 

That’s enough soap-box for now. 

I love you, talk soon, and I will see you June 7th :).


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