What I learned pivoting from passionate founder to compassionate CEO

Challenge Factory’s Blog

A woman hiking through a forest
A woman hiking through a forest

What I learned pivoting from passionate founder to compassionate CEO

Challenge Factory’s Blog

By Lisa Taylor

“I love working with entrepreneurs,” a friend told me recently. “They’re always so passionate about the work.”

He explained that, in his corporate career and with his clients, the passion tends to be for the business, not the subject matter. There’s a distinct difference between a career dedicated to building a thriving business and one committed fully to the subject matter of your work.

I should know. I’ve done both in my career.

Are you passionate for your business’ success or your business’ work?

My corporate IT career was completely focused on seeing the business succeed. As I rose through the ranks, I managed larger and larger teams and oversaw increasingly complex projects, portfolios, and P&Ls.

Despite this, I didn’t have a technical background, the skills, or, frankly, the interest to be passionate about the actual work we did. Instead, I cared deeply about the clients, my team, our processes and results, and my superiors’ demands. That we built data centres, architected backbone infrastructure, implemented storage solutions, and streamlined IT service processes didn’t matter to me as long as we outperformed our competition.

When I left corporate life to launch my own business, my focus and passion shifted. I cared more about the impact of the work than the growth of the business. I became the entrepreneur my friend was talking about, gaining recognition for my expertise rather than my managerial acumen.

Not all entrepreneurs and founders are this way.

My father built a very successful tutoring and then adult education business by being passionate about the business, not the work. As the business grew from one to nine locations, people often commented on how passionate he was about learning.

But I knew the truth. His team was passionate about the work. His drive was to build a successful business.

Each decision we make changes us

The conversation with my friend helped me understand how changes in Challenge Factory are reflected in my own growth. As Challenge Factory enters its next stage of growth, my focus and passion as founder are shifting again.

I remain fiercely committed to our work and a passionate advocate for its impact. But my best days are when our work drives our presence into new markets, adds larger impact projects to our portfolio, establishes new relationships, and secures what’s needed to fuel sustainable growth.

The conversation with my friend started with him asking me if I ever wondered what would have happened if I’d stayed in my corporate career. It’s the kind of question that has no real answer.

Each decision we make changes us, and our career path, just as the world continues to change too. I’m not the same as I was in my 30s when I stepped into entrepreneurship. And just because I’m now in my mid-career doesn’t mean I’m not still growing and pivoting.

Business strategy and career development intertwine to drive impact

The difference between entrepreneurs who excel in their field and those who build successful businesses often lies in where they focus their passion: on the work itself or on business growth.

Few can do both and almost no one can do both at the same time. It’s why common wisdom says founders who can’t be as passionate about business growth as they are about the subject matter should bring on CEOs to run the business when it hits certain growth thresholds.

Brian Chesky, co-founder of Airbnb, has challenged this advice. He points out that founders run companies differently than managers, and they can succeed by staying in “founder mode” instead of trying to switch to manager mode.

Challenge Factory is on the threshold of several projects that will propel us into the next stage of our growth. I’m fired up for it, even as I fight the urge to be involved as deeply as possible in every project and with every client.

If my friend and I meet for lunch again in five years, I wonder if he’ll ask what would have happened if I had chosen not to pursue our active growth strategy. Choosing not to grow Challenge Factory would not only be about the future of company. It would also limit the career opportunities for the team, including me.

This leadership choice has put me on the threshold of my own new career pivot, from founder to CEO. It’s an important moment of healthy career development for me that cascades into opportunity for the entire team. I’m reassured to learn from Chesney that while there are new challenges ahead, what made me a strong founder will continue to serve me well.

Before Challenge Factory’s growth strategy was officially set, I presented it on a team call and emphasized that growth is a choice. (This is another example of founders ignoring formal hierarchy and working directly with whoever can help solve the problem.)

The team’s response on that call and in follow-on demonstrations of passion and commitment is how I know we’re all-in for what comes next, both for the business and for each of our careers. Business strategy and career development intertwined to drive greater impact at all levels.

Thanks for being part of Challenge Factory’s growth journey.

Are you a leader going through a career pivot or transition? Explore Challenge Factory’s talent and leadership advisory services, and let’s talk about how we can help.