How Do I Make This Fun?

Read time: 6 minutes

Welcome to The Ascend Archives Tuesday Tale, 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.

“How do I make this fun?”

This question has changed the way I live over the past 8 months.

It feels silly writing that but it’s true. Most cliche sayings make me cringe and I believe there’s a line of consuming too much ‘self-help’, but there are some lessons I agree with. “Life is about the journey, not the destination” and “If you aren’t happy now, no amount of money or success will make you happy” are two that have stuck with me.

With these in mind, I have tried to live intentionally in 2024 by doing what I enjoy and finding ways to do the things I don’t enjoy in the most fun way possible. I don’t have a great way to quantify it, but I believe this has led to one of the happiest years of my life.

The easiest way for me to implement this is by asking myself that question I learned from Ali Abdaal: How do I make this fun? It can be applied to any situation: large or small.

Examples of Making Things Fun

Strength Training: I have struggled with this for years. I could never stick to a routine and didn’t enjoy keeping track of all my reps and what workouts to do.

• How I made it fun: I found a local gym in Austin (shout out Athletic Outcomes) that does group strength training classes. It’s a no BS, 45 minute class that has 4 exercises (2 push and 2 pull). They create a positive atmosphere and it takes the “work” out of me figuring out what to do. I just show up 3x per week and get stronger.

My Career: Work isn’t always going to be fun. My previous job in consulting included dozens of meetings, nonsense trainings, administrative requirements, and travel to annoying places. My previous job as an Executive Assistant included commuting 2+ hours a day and living in a city I didn’t like.

• How I made it fun: I chose to work for myself which allows me to make my own schedule and avoid corporate red tape. On Mondays and Fridays, my calendar is completely open so I can work on whatever I want. I also chose work that I can do from anywhere in the world. My commute is now a 5 minute drive to my local coffee shop (or in today’s case, the Zanzibar beach overlooking the Indian Ocean).

Networking: I enjoy having conversations with interesting people so I try to talk to at least 3 different people each week. But sitting behind a computer all day and talking on Zoom gets exhausting.

• How I made it fun: I meet with people in person. Every Tuesday, I work from the same coffee shop and hold “office hours” where I will invite people I’ve connected with to come meet me if they are available. When that’s not an option, I opt for phone calls instead of Zoom so that I can go for a walk in my neighborhood or by the lake while we catch up.

Dating: For the first year of me dating, all of my first or second dates would be at a bar. We’d order a beer or two, sit across the table from one another, and pretty much interview each other to see if we’d be a good fit. That’s just what I thought you were “supposed” to do. I dreaded these dates and also wasn’t very good at them.

• How I made it fun: Instead, I thought about the activities I enjoy doing and decided just to invite my date along. We grabbed a smoothie and went for a walk around the lake, we cooked homemade pizzas, and we went to a cool Omakase dinner. It was a lot more fun and worked out a lot better.

Getting blood taken: I HATE getting my blood drawn. It freaks me out and I get super anxious. But it’s something I gotta do.

• How I made it fun: Now when I enter the room to get my blood taken, I make a joke with the nurse. I’ll say “I know I’m 28 but I’m still terrified of this, can you talk with me to keep me distracted”. The lighthearted joke eases my nerves and it helps to talk about random stuff instead of sitting in silence thinking about the needle in my arm.

Putting It Into Action In Real Time

On Day 3 of hiking Kilimanjaro last week, I was hitting a wall. My friend Tim was struggling with symptoms of altitude sickness, we were both running on very little sleep from jetlag and camping, and doubt was starting to creep in as to whether I could make it to the top.

Vibes were low.

Then something happened that prompted me to ask the question: “How do I make this more fun”?

If you read my last newsletter, you know that this was a serious hike. I was completely focused on taking one step at a time and making sure my mind and body were ready for the trek. But taking it too seriously was making me anxious. Sure, the conditions were tough and I was doing something hard, but how could I make this experience more enjoyable?

The trigger happened during hour 8 of a 10-hour hiking day. The sun was strong and we were low on water. Charlie, our guide, decided we needed a break. We took off our bags and laid down in the shade. It was quiet for a few minutes until Charlie broke the silence, “Do you guys know Adele?”

It took Charlie a few tries at pronouncing her name in his broken English, but eventually Tim says, “Adele? Like the song Hello”?

“Yes!!”, says Charlie.

I look at Tim and laugh, “Yes we know her”.

Charlie starts playing Hello from his phone and a few minutes later Charlie and I are shouting:

“Hello from the outsideeee”

“I must have called a thousand times. To tell you I'm sorry for everything that I've done…”

For a few minutes, I forgot all about the altitude, my tired legs, and my lack of sleep. I was having fun with my friends, singing an absolute banger.

From that moment on, I knew the rest of the week was going to be challenging but I was going to find ways to enjoy it.

I picked up the chatter on the hikes with Charlie and Tim. We learned that Charlie’s favorite animal is an impala. When we asked why he said, “Did you know male impalas can have up to 100 female partners?” It then became our inside joke that Charlie was a lady’s man and had 100 girlfriends.

Then, on the night before we summited, I found an old playlist saved on my phone from when I ran the Austin Half Marathon. I played Til I Collapse by Eminem and We Own It from The Fast and Furious movies on repeat to get myself pumped up for the final push to 19,000 feet.

These small but meaningful shifts not only made my time on the mountain more fun but helped me get in the right mindset to make it to the top.

Asking this question about fun sounds super simple but it works. When I think about how to make things I’m doing more fun, I enjoy it more and am better at getting it done. It usually doesn’t take that much more effort, but just the awareness makes all the difference.

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