Something Is Missing In My Ideal Day

Read time: 4 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.

It’s 9:30 PM on a weekday in April.

My evening routine starts by pulling out a notecard from the stack in my nightstand. I jot down 3 things I’m grateful for. Then I start thinking about my 3 priorities for the next day.

I look at my calendar. It’s completely blank. No meetings, phone calls, appointments, or social events. The entire day is open for me to do and work on whatever I wanted.

So I zoom out and think about the different projects I’m working on and begin time blocking my ideal day. I decide on this…

I follow my schedule and enjoy the day. I completed paid consulting work, I wrote my newsletter, I worked out, and I got space to think and learn. How could it get much better than this?

A Question From Sahil

Sahil Bloom shared in his newsletter 7 Questions that changed his life. One of them was “If I repeated this day for 100 days, would my life be better or worse?”

So I asked myself this question about that random Thursday in April…

The short answer is my life would be better.

But when I dig into it, the structure of the day is there, the deep work is important to move things forward, the exercise will keep me healthy, and the space is key for my mental health. But something important was missing.

Riffing with my Board of Directors

For the past two months, I’ve been exploring the idea of helping creators build the business side of their brands.

There are thousands of creators out there with hundreds of thousands of followers, but the creators don’t know how to effectively monetize the audience they’ve built. They either don’t have the business skills or don’t want to spend their time learning the skills. They need help.

Last Thursday, I sat in the Austin Central Public Library and dumped all my thoughts into a Google Doc. Everything I’ve learned from consulting for Fortune 500 companies, working as a Chief of Staff to a creator entrepreneur, ghostwriting for creators over the past 5 months, attending a creator conference in Boise, and listening to upwards of 100 podcasts on the creator economy. What resulted was a very rough draft of a startup business plan.

I was so amped up about the opportunity that I had to share it. So I sent it to 2 of my best friends (a tech private equity guy and a startup founder). They immediately offered to hop on the phone with me the next day to discuss.

Not only are they great friends but they are incredibly smart and business savvy. They are a part of my “board of directors”. A group of people who I can turn to for different parts of my life. I have my go-to people for fitness, for dating advice, for real estate investing, etc.

But for brainstorming business ideas, these are my guys. They reviewed my “business plan” and gave me honest feedback. They shared examples of other companies they have seen in the space, pushed me to think more critically about my value proposition and the niche I would serve, and suggested ideas or questions for me to further pursue.

I left these hour long thought provoking discussions energized and ready to find solutions to the unanswered questions.

Final Thoughts

These conversations helped me realize what I was missing on that Thursday:


I love the autonomy of designing my own schedule. I love having space to think, to read, and to write. But that all involves working alone.

There’s a lot I don’t know. There’s a lot of things I’m not good at. So there’s power in getting different ideas and perspectives.

It brought me back to my EY days. I was on projects where I had no interest in the subject matter, had to travel to the middle of nowhere, and hated the clients I worked for. But my team made the experience positive. I enjoyed being around these people. We were working on solving challenging problems. We were in it together.

I miss that feeling.

So I’m going to lean into finding that feeling again. Maybe it’s more conversations with my “board of directors”. Maybe it’s finding a partner to build this business with. Or maybe it’s just hiring employees.

Time will tell. But I know that if I figure out how to add collaboration into my day and repeat it 100, my life will be 10x better.

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!