2018 was a huge year for me. I made some big decisions, saw some amazing places, and made countless memories with friends and family. Here are some of the biggest things I learned over the past 12 months.

1. I wasn’t aggressive enough in pursuing my future in prior years

I was at my consulting job for 5 years. At first, my plan was to transfer from DC to NY, but I loved DC so that didn’t happen. I already had a Master of Management from business school and didn’t plan on going back for an MBA. I thought I’d find a startup to join but didn’t fully commit to that. At one point in 2014/2015 I interviewed with a few tech companies in NY and SF but nothing panned out.

Then it got to a point where I was on auto pilot. Work had cycles of being rewarding and then soul crushing, but I had amazing friends and a great life. I didn’t have enough of a fire under my seat to make real moves, but I should have.

I turned 29 last March. This was a huge reason why I made the leap this year to pursue golf. I’ll be 30 soon and that’s pretty scary for me. If you’re interested in learning more about the significance of beginnings/endings/anything related to timing, take a look at Daniel Pink’s “When.” Super interesting. Long story short, I was more motivated to make a change, so I did.

I should have been more aggressive in pursuing my future a few years ago. I could have had just as much fun but been more intentional with my plan. Better late than never, and now my foot is on the gas pedal.

2. My biggest fears about leaving my job to pursue a dream were gone a few months into the journey

Before I decided to pursue golf, I considered taking a LOA to travel the world. I started thinking about this in 2014/2015 but didn’t take any action. There are many different reasons to leave a job (travel, pursue a dream, start a company, etc), but I think a lot of the fears we have are the same:

I wouldn’t be maximizing my professional growth if I stopped working.

Promotions and raises? I have a new definition for professional growth now. Where do I want to be in 2, 5, 10, 20 years? If I keep advancing down a path that I don’t want, is that making progress? If I advance slightly slower because I take some time to re-evaluate my future, isn’t that maximizing my professional growth?

All of my peers will be advancing in their careers while mine is on hold.

You won’t be promoted after you leave work and your friends and coworkers will continue to advance. That’s okay. While you won’t be advancing in the career you had, you will be gaining additional perspective, have time to learn new things and meet new people, and will advance your LIFE. By not making a change, you are giving all of this up.

I wouldn’t be able to afford it.

This is just planning. Take some time to write down how much what you want to do will cost. Save enough to make it happen by reducing your expenses before leaving.

What if I fail?

Most of the time, we can go back to what we were doing before or at least something similar. Trying new things brings new knowledge, experiences, and networks that you wouldn’t otherwise have. I might have a better shot at winning the lottery than becoming a pro golfer, but I know the odds. I want an exciting life. It’s hard to truly impress and excite yourself if you don’t try things where failure is strong possibility.

Additionally, check out Tim Ferriss’s 13 minute Ted Talk on Fear Setting. It’s had a huge impact on my mindset. To summarize it in one sentence, “we suffer more in imagination than in reality.”

https://tim.blog/2017/05/15/fear-setting/

3. If you don’t know exactly what you want to do in the next few years and beyond, it’s okay to throw a bunch of stuff at the wall to see what sticks

I knew I wanted to do something different but wasn’t sure what. In the spring of 2018 I gave myself a date of November 1, 2018 to make a move and I picked golf.

While this is my focus, I also have a lot of time to work on plan b. What is plan b? I’m not sure yet, but it’s going to be one of the dozen other things I’m working on this year. Making time for a few different things is difficult but I’ve made it work by blocking space on my calendar.

If you don’t know what you want to do (but know you want to do something different), make a list of things you might want to do and actually start one! Write the book about your experience, produce a beat and post it to your Soundcloud, or start volunteering. If one fails, move on and pick another!

For years I’ve kept a list of business ideas and projects in my phone and, until recently, they were just ideas. You don’t need to leave your job to start a passion project or business, but you do need to carve out some time for it.

2019

Getting better at golf, and much more. Big things are coming, stay tuned!

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Moving to a new city as an adult isn’t easy. It’s hard enough finding your way around and getting used to a new routine. And to really enjoy the place you have to make friends.

My brother and me in Savannah (en route to Florida) with some locals we met in a park

A couple weeks ago I moved from DC to Florida for the winter so I could play golf every day and try to go pro. I’m staying at my parents apartment and my 24 year old brother made the trip down with me. The community is mostly made up of retirees and the average age is above 70. We were eating lunch when an older dude sat next to us at the bar and started chatting. Before we even exchanged names he welcomed us to the neighborhood and invited us to dinner with his wife and another couple that night.

It would have been easy to come up with an excuse to decline but we accepted and had a great and unique experience.

A quick thank you

I just wanted to thank everyone who goes out of their way to help make others feel welcome. Personally, I have been extremely fortunate to have met many who have invited me to dinners, parties, vacations, events, and countless other activities that have made great memories. It is because of you that I have had such a good time in my post-college life.

Try to have unique experiences

I’m a HUGE believer in having unique experiences. Ever since I moved to DC 5 years ago I’ve tried to be a “yes” man as much as possible. Unique experiences are easier to remember, stand out, and make life more exciting.

Sometimes it’s a trip to the UAE with a couple friends and some others you don’t know when you find a glitch $200 round trip flight. Other times it’s going as a plus one to a roommate’s Tinder brunch date on 10 minutes notice. We are primed to say “no, thank you” when there’s an unexpected invite, especially when we don’t have the time to think it through. But saying “yes” to these has created some of my best memories.

Unique experiences don’t have to be expensive trips or odd activities

Tough Mudder group picture — A few weeks after I moved to DC I did a Tough Mudder with my friend, Sean (green shorts), and met Jon (next to me), who is now a great friend

Something as mundane as eating dinner with new friends can be a unique experience. But it could be something as simple as going to a party where you only know 1 person, going to karaoke with a random group you met at a bar, sitting next to someone at the coffee shop instead of alone, cooking something new with friends, signing up for a Tough Mudder, or even pulling over during your commute to watch a great sunset.

Back to my dinner – How many times have you eaten with someone 40-50 years older than you, who wasn’t a coworker/boss, relative, the relative of a friend, or the friend of a relative?

In each of those situations, the other person has a persona to fit into. But because we had no outside connection we let our guard down and hung out in a way none of us had ever done before. Politics, travel, regrets, changing policies, and life achievements/goals were all discussed. They even invited us to their apartment after dinner for dessert and coffee, and to introduce us to their dog!

People in their 20s can really be friends with those in their 70s.

Making Friends

The easiest place to meet people is at college. Everyone is your age, at the same stage of life, doing the same activities, and you all live together.

But it gets harder as you get older.

When I moved to DC, at 24, I only had a few friends. They were all in their last year of law school and had their own friends. My roommate was also new to DC and in a similar situation.

Volleyball team picture — Almost all of us were randos who were assigned to the same volleyball team. 3 years later we are still together and I have to miss playoffs next week!

I quickly realized that if I wanted to have fun in the new city I needed to meet as many people as possible. I started meeting people on the basketball court at the gym, parties, and through friends of friends of friends. We went to each other’s friends’ parties, joined intramural sports leagues, and went to each others’ work happy hours.

I had always had similar friends growing up and in college. There’s nothing wrong with that, but in DC I started meeting people who were different. They were older/younger, had different careers, different backgrounds, etc, and it was amazingly eye-opening to spend time with people who have different experiences than me. They see the world differently and gave me additional perspective, in addition to a larger pool of potential friends.

Birthday picture — Before I moved to DC, I only knew 2 people in this photo, taken on my 27th birthday.

Be “down” and inclusive

When you’re post-college and trying to make new friends it’s different than building a bond over a decade or 2 as a child. You aren’t forced to see these people every day in school and your parents don’t organize playdates. People are also much busier, so there are fewer opportunities to hang out.

That’s why its super important to be “down.” People like those who are willing to do things with them. This is how you get invited to the next thing. And if you keep declining offers they will stop coming!

I felt a little awkward when that first dude in DC invited me over to hang out with him and his girlfriend 2013. Jon and I had just met a few days earlier, but now he wanted me to come over to his apartment? What a weirdo! But I went.

That hangout turned into countless dinners, activities, trips, and new friends. He ended up becoming one of my best friends and I was even a groomsman in his wedding a few weeks ago.

Groomsmen Photo — I met Jon at the Tough Mudder when I first moved to DC. I was recently a groomsman in his wedding.

Accepting invitations is great, but extending invites is even better. It feels great when someone invites you to something even if you don’t want to go. Make people feel wanted and invite them, especially when there’s no cost. Have BIG birthday parties and invite those random people who you once exchanged numbers with but never ended up hanging out. Invite that guy you like but aren’t close with to watch the game when you were planning on watching it alone. It helps you build a relationship and makes it normal to chat more often. Soon you’ll have friends for all activities in your life; gym buddy, fellow foodie, sous chef, single going-out PIC, etc.

Summary and takeaways

Moving to a new city has a lot of challenges, but making new friends and enjoying your time shouldn’t be one of them. Hopefully I’ll be able to write a similar post about my new friends in Boca in a few months!

Try to have unique experiences because they are more memorable, fun, and make life exciting.
Be “down” when you get invited to things, even if don’t think it will be super interesting. Most of the time you’ll be glad you went.
Invite your new friends to hang out and participate in activities, even if you don’t think they would want to go. Everyone likes to feel wanted and sending an invite is an easy way to do that.