Life as a Solopreneur

Read time: 5 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.

The Corporate Life

Over 5 consecutive days, I saw no more than 2 total hours of sunlight.

I was camped out in a windowless executive board room from sun up to sun down. The only fresh air I got was on the 2 minute walk from the hotel and the occasional 10 minute break in between meetings. By the time I closed my laptop each day, the only thing on my mind was my bed.

So much for the glamourous business trip to London.

I went to London with my teammates Haley and Doug to run workshops with executives from all across Europe. These executives each oversaw $10M-$50M budgets for a $50B+ organization that was in the midst of an M&A deal that would change the landscape of its industry.

Haley, while more experienced than me, didn’t know the workshop content like I did. Doug, the department leader, was the figurehead and mainly there to schmooze with the client. So that left me. A 26-year-old kid to lead 5 days of workshops with millions of dollars on the line.

No big deal.

Each day I led the meetings as leaders from Italy, Germany, Amsterdam, and the UK filed into the boardroom. Haley had my back taking detailed notes, chiming in with architectural insights from her previous career, and leveraging her charismatic personality to make the client feel at ease. Doug did his thing by kicking off each meeting with an engaging story and coming to the rescue when the Dutch clients reaming us out for “not knowing what we are doing”.

Each night, Doug, Haley, and I would get a nice dinner by ourselves or with the clients. We would take a break from the chaos of the day and discuss our lives outside of work. After dinner, Haley and I would go back to our hotel rooms and finalize the next day’s slides and financial projections. Each morning, Doug, Haley, and I would regroup for breakfast in the hotel lobby to strategize and make final adjustments for the day’s meetings.

By Friday at 7 PM, I remember feeling completely drained and exhausted. But I somehow managed a smile while Haley and I explored the state-of-the-art EY headquarters.

Solopreneurship

Decisions come with trade-offs.

I decided to trade in my corporate life for entrepreneurship. I traded structure for freedom, governance for autonomy, stability for uncertainty, and teamwork for working solo.

Freedom

I get to design my day however I want.

Friday through Monday are my Deep Work days. I don’t schedule any meetings or phone calls for 4 days straight. This allows me to get long stretches of writing and creative work done without worrying about preparing for a meeting or thinking about what topics to cover on my next networking call.

Tuesday through Thursday are my Collaboration days. These days are filled with client meetings, mastermind groups, coaching, and networking calls. This allows me to be flexible with call times because I know that in between calls I’m just going to be working on admin stuff that can be moved around. This way when people are late or don’t show up for calls, it doesn’t impact my creative flow.

Autonomy

I get to choose what I want to work on.

No more office politics and schmoozing with Partners to get on the best consulting projects. I get to decide whether I want to work with a client and what exactly I work with them on.

Uncertainty

There are no guaranteed paychecks.

It was nice knowing that every other Friday I was going to get the same amount deposited in my bank account and that every year I would get a bonus and a raise. But as an entrepreneur that’s not the case. All of my clients are on 1-3 month contracts. So I’m one mistake, one economic downturn, or one negative thing happening in my client’s business away from losing a portion of my income next month.

Working Solo

It’s me against the world... which includes a lot of time spent in my own head.

There’s no hopping on a Zoom call or into a conference room with colleagues to brainstorm solutions to a problem. There are no team dinners to laugh about the stupid stuff that happened that week at work. There’s nobody else in my meetings to have my back when I don’t know the answer to a question.

I have to be a jack-of-all-trades. Come up with the business strategy. Make the sales. Do the work. Answer the questions. Deal with the issues. I need to constantly have my shit together.

Final Thoughts

While I have my business coach and my board of directors who I can lean on when issues come up, it’s not the same as having teammates. People who are in the trenches with me. People who are with me working towards a common goal.

I wouldn’t have been able to lead those London workshops if it wasn’t for Haley and Doug.

So that makes me wonder, what else can I accomplish in my current business if I wasn’t doing it alone?

The value of a team is not just in the work but also in the connection.

Last Wednesday in Costa Rica, I had a Zoom call with a creator I met at a conference. After an hour of talking about his business, he asked if I wanted to help him build out a membership community. He said I could use it as a case study for future clients. Plus if it goes well, he would pay me to help run it.

This was the perfect opportunity to help me transition from just a creator ghostwriter to a creator operator. So I jumped on it.

Later that same day, I was walking in downtown Tamarindo and I got a text from another potential client…

“Been a crazy couple of weeks, sorry I haven’t gotten back to you. Let’s start with the $1,600 per month and the revenue share”

I just landed a client I thought had gone with someone else!

All I wanted to do was celebrate with someone…to get together with a team to figure out how the hell we’re going to deliver quality results to double the amount of clients overnight.

But I have no team. There was nobody to turn to.

So as the afternoon thunderstorms rolled in, I ducked into a local cafe overlooking the Pacific Ocean. I bought a beer, soaked up the win, and started brainstorming solutions to this problem... On my own.

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