From Corporate Treadmill to Entrepreneurial Freedom

Forging your own path to taking back control

Have you ever felt like a chess piece on someone else's board, moving according to rules you didn't set?

I've been there and want to share my journey from corporate executive to entrepreneur – a path that's challenged everything I thought I knew about success, fulfillment, and living life on my own terms.

For years, I climbed the corporate ladder, transforming businesses with cutting-edge technology:

• Revolutionized executive reporting for a top UK finance company

• Scaled digital marketing to 8,000 analysts at a major US company and transitioned it to the cloud

• Built a real-time web analytics platform enabling AI-driven personalization for millions

Sounds impressive, right? But here's the truth bomb: as I ascended the corporate ladder thanks to all this success I led, my dream job slowly morphed into a nightmare.

The Corporate Game: A Reality Check

Managing employee performance is a significant part of corporate life.

On an annual cycle employees are stack-ranked and, through various methods, the lower performers are encouraged to seek employment elsewhere.

I used to defend this process and do everything possible to make it as fair and supportive as possible. But here's the kicker: the process's priority is increasing the talent at the company rather than supporting all individuals.

As an employee, you're the product of the process, not the customer of it.

Additionally, those denoted as higher performers receive differential bonuses at the positive end of the process.

While this might mean an upgraded vacation or some home improvement for junior employees, these higher ratings can be worth hundreds of thousands of dollars per year in additional compensation in the executive ranks.

We all think we are not sneaky and wouldn’t undermine our colleagues, but everybody has a price, and you see that play out in many ways. I don’t blame anyone for the behavior the system creates - it’s human nature.

Think of game shows or reality TV where contestants build secret alliances or engage in very devious behavior to win prizes of way less than six figures. We expect it, and we laud them for it.

The resultant view behind the executive curtain isn't always pretty. This system creates fundamental cognitive dissonance in corporate life. Leaders preach care, teamwork, and support, but their individually motivated actions can often tell a different story.

For some, it’s a game in which the prizes on offer might not be worth winning, given the personal sacrifices required to secure them.

I needed a different path.

Breaking Free: The Entrepreneurial Leap

In July 2024, I resigned from my executive role at one of the biggest US banks. Was it scary? Absolutely, but it was necessary.

The impact of the transition has been eye-opening:

• My health has improved dramatically

• My relationship with my kids is twice as good

• I've rediscovered my passion for delivering high-impact change

Now, I'm building two AI-powered businesses:

1. Crawford McMillan: Helping mid-market companies to transform their key processes with AI

2. DMV Digital Marketing: Assisting nonprofits in maximizing Google Ad grants and boosting support for their missions.

Starting your own business brings many challenges with it - a different type of hard - but they are challenges that I am much more excited about meeting.

The Unexpected Benefits of Going Against the Grain

Since starting, I’ve already realized some significant personal wins.

Reclaiming Your Time

I've settled into a routine that works for me:

• Mondays for content creation

• Tuesday to Thursday for client work

• Fridays for learning and keeping up with AI advancements

• Saturdays for substack and kids sports

• Sundays for untouchable personal time

The best part? Nobody's telling me what to do. I'm no longer a chess piece on multiple chessboards.

Redefining Success

It turns out I don't need huge houses or flashy cars. Controlling our family’s monthly burn rate has allowed me to build this business on my own terms. I'm focused on creating something sustainable, automation-first, and scale-first.

Prioritizing Health and Relationships

Stepping away from corporate life has dramatically improved my health and family relationships. I even completed an indoor triathlon recently!

Embracing Authenticity

I've had to unlearn the corporate habit of pretending to be productive all day, whether you are or not - you've got to manage that personal brand! Now, if there's not much going on, I'll hit the golf driving range or watch Netflix without guilt. It's liberating!

Challenge Your Beliefs

Question the norms. Just because "everyone" follows a particular path doesn't mean it's right for you.

• Prioritize yourself. A company will never care about you as much as you care about yourself.

• Define your non-negotiables. Everyone's willing to sacrifice different things – time, ethics, personal judgment. Figure out what matters to you.

• Embrace discomfort. Growth often lies outside your comfort zone.

• Redefine success. It's not always about the biggest paycheck or the fanciest title.

Whether you're committed to staying corporate or thinking of making the leap, make it work for you, not the other way around.

It's okay to go against the grain if it means living a life that aligns with your values and aspirations.

Are you ready to challenge your beliefs and reshape your perspective on work and life? What's one small step you can take today towards living life how you truly want to?

Here's to forging your own path.