Living Life By Design

Read time: 8 minutes

Welcome to The Ascend Archives, a weekly newsletter where I share a story about a transformation, revelation, or change in thinking that has helped improve an aspect of my life. Today is the second essay from my writing cohort, Write of Passage. Thanks for reading!

The ground beef is sizzling on the stove. I’m crushing avocados for fresh guac. The rice, beans, cheese, and lettuce are ready to go for taco night. 

I’m excited to surprise my fiancé with a home cooked meal amidst our hectic lives. 

I was in the middle of 60 hour weeks working towards an early promotion and big pay raise. My fiancé recently gained the courage to quit her unfulfilling engineering job and pursue her dream of becoming a doctor. Our time not working or in school was filled with social events with friends, walks along the lake, weekend trips to visit family, and date nights at our favorite spots. We had the house, the dog, great career paths, loving families, supportive friends, and a dream wedding planned. Everyone couldn’t wait for the high school sweethearts to finally get married in 4 short months.

Just as I started to warm the tortillas, the door to the apartment burst open. 

My fiancé walks into the kitchen and drops to the floor without saying a word. Tears flowing down her face uncontrollably. I run over to her. Our anxious dog Charlie starts barking up a storm. I wrap my arms around her and ask what’s wrong. She can’t make out any coherent words.

I tell her just to breathe. “It’s going to be okay”.

She continues to cry without saying a word.

I grab her a glass of water and again say, “It’s going to be okay”.

Then she musters the strength to say, “It’s not going to be okay”.

“What do you mean? Just control your breathing and this will pass. Whatever it is, we will get through it”.

“It’s not going to be okay,” she repeats.

“Why?”

“Because you’re not the one for me. I can’t marry you”.

–

Until that night, I had never faced true adversity. 

I grew up with loving, supportive parents. I got straight A’s. I attended my first choice for college. I graduated with no student debt and a prestigious consulting job. I never had to go on an awkward first date. I was a healthy 26 year old guy checking off all the right boxes. 

Then life yanked the rug right out from underneath me. Every day for 10 straight years, I spoke to this person. Suddenly that disappeared. The vision for my life over the next 50 years? Shattered.

Who was I without her?

Answering that question had to wait. Because all of my friends and family were finalizing their plans to celebrate with us in a few months. 

I couldn’t tell all 200 people invited personally but I wanted to be the one to tell my best friends. So on a random Tuesday, I made a group chat with 10 of my closest friends. I asked if they could join a FaceTime call so I could update them on something difficult I was going through.

Everything was still so fresh. I was questioning why this happened to me, how I fucked this up, and where the hell did I go from here. While I had zero answers, I did know that the wedding was off, I was in a dark place, and I needed my friends for support. 

As soon as I saw all my friends on the call, tears started flowing down my face. I took a deep breath and gathered myself. It was the first time I was saying the words out loud, “I wanted you guys to hear it from me. It’s over. We broke up and we’re not getting married. I appreciate you guys so much”. That was all I could get out before bursting into tears and saying I’d fill them in on the details later. 

In the weeks that followed, I picked up Ryan Holiday’s Obstacle Is the Way - the perfect book at the perfect time. When I read the Marcus Aurelius quote, “What stands in the way becomes the way”, I realized I couldn’t change what happened, but I could decide how to respond. I could hole up in my parent’s basement feeling sorry for myself or I could take advantage of this new freedom to answer that question, who am I?

I chose the latter. 

In my old life, I was tied down. Every decision was made through the lens of us, not just me. Could I start a business? Nope, someone had to pay the bills. What if I took a risk on a startup? Nope, we needed to save for future kids. Could we move somewhere warm? Nope, we gotta wait to see where she got into med school. 

But in my new life? Nothing was holding me back. The weight of all these responsibilities was lifted from my shoulders. 

I started asking myself questions that I could finally answer as my authentic self.

If I could live anywhere in the world, where would I go?

If I could do anything for work, what would I do?

If I didn’t have to work at all, what would I do?

Not only did I start thinking about these questions but I took action to find the answers.

I left Chicago and moved to Austin -  a city where I didn’t know a soul, but knew that I could spend the majority of the year outdoors and be surrounded by a young, entrepreneurial community. I quit consulting to pursue my entrepreneurial itch. I started traveling to my bucket list destinations all over the world - 2 weeks hiking in Patagonia, 2 weeks eating through Italy & Spain, and a full 6 week sabbatical to Australia & New Zealand. 

Without the weight of my previous obligations, I found space. Space to think about what I value, what I enjoy, and what I truly want out of life. 

For the first time, I defined my values: adventure, growth, relationships, contribution, and authenticity. I wrote out a 3 year vision of the type of work that excited me, what my ideal week looked like, and who I wanted to spend my time with. I shifted my mindset from having a specific roadmap to being open to the unknown. I had to start thinking like a scientist and experiment to figure out what I wanted and where I wanted to go. I had to be okay knowing that I was going to fail, I was going to run into roadblocks, and there was no timeline for when I would figure it out. 

The Experimental Mindset 

Finding work that I enjoy

I was done with Corporate America, but I didn’t know what was next. My first thought was to buy a business. I saw the gurus online who bought small businesses, improved the operations, and started printing money. After 5 years of consulting, I could certainly figure out how to turn around a small business. However, after 3 weeks of analyzing deals, I realized that owning a local business did not align with my desire for autonomy, freedom to work from wherever, and impact-driven work. I continued experimenting until I came across ghostwriting for creators. The moment I wrote a client’s newsletter from the beach in Costa Rica that helped readers make positive changes in their lives, I knew I was on to something. 

Finding my community

I wrote out a list of activities I enjoy doing: playing basketball, training for triathlons, writing, and having conversations with interesting people. Then I leaned into these things that brought me joy. I found a group of entrepreneurs who play pickup basketball twice a week, writers to discuss my writing with at a weekly writing club, and runners who take running seriously but not too seriously at a local run club. These are activities that I never prioritized in my old life, but have unlocked fulfillment and dozens of new friends who bring me energy. 

Finding my life partner

When I first started dating, I defaulted to my old mindset. I assumed that first dates had to be grabbing a drink. We’d meet up at a brewery, sit across the table from each other, and take turns asking questions. I would second guess every word and focus on whether she “checked the boxes”. After months of dreading first dates, I realized I needed to forget the “right” way to date and do it my way. I started planning dates doing things I enjoyed like grabbing a smoothie and going for a walk or cooking dinner together. It not only weeded out girls who wouldn’t fit well into my lifestyle but I was able to show up more naturally and be myself. 

Final Thoughts

These days, you can catch me playing pickup basketball, co-working with interesting people at various coffee shops, training for triathlons, taking epic trips to Africa, and continuing to challenge myself physically, mentally, and emotionally. 

I was living a life that I thought was great because it checked all the boxes. But I learned that what really matters is living life with intention - a life doing what I enjoy with the people I love.

That’s living my life by design - one that I’ll have no regrets about when I’m on my deathbed.

Thank you for reading! As always please reply and let me know what resonated, what didn’t, or what you question. I love chatting about this stuff!

Cheers,

Andrew