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Bold Type: When Avoiding Risk is Risky

Bold Type: When Avoiding Risk is Risky

Who doesn’t love a good business success story? The kind with a challenge so daunting, it takes a special kind of leader to overcome it. She uses her ingenuity and willpower to see the problem in a different light and charges a new path forward. Those efforts compound and inevitably lead to the remarkable company we see in headlines today.

That story, while captivating, is usually far from the truth — it suggests a clear, visible path to success that doesn’t exist, and misses the perspective of the leader doing the work in the moment. What seems inevitable in hindsight is highly questionable at the outset. The fact is, when you’re setting out to do something different, things usually seem chaotic, unpredictable, and risky.

Yet, these leaders move forward, often going against conventional wisdom or the more familiar and comfortable status quo. They draw strength from conviction and a deep desire to see change happen. They turn that energy into courage to act, without knowing what the outcome would be.

We call these daring leaders Bold Types.


What does it take to be bold in business?

In times of uncertainty, it’s easy to seek comfort in the knowns. But in business, that sense of security often comes at the expense of innovation. (In other words, avoiding risk can be risky in itself.) So, how can leaders embrace the unknown and uncomfortable and challenge the status quo in a way that brings them closer to their vision?


Play The Long Game

Is there any challenge as daunting and complex as wealth inequality in the United States? On average, white households have a net worth 4x greater than that of Black or Hispanic households… even though they only comprise 64% of the population. Generational wealth perpetuates this pattern — but when asked how to address it, many would throw up their hands.

Karla Trotman, on the other hand, sees this as an opportunity. Karla is the President and CEO (and second-generation owner) of Electro Soft — the nation’s largest Black-owned electronics manufacturing and engineering firm. She sees small businesses as crucial structures of economic stability, empowerment, and wealth creation for our nation’s most marginalized groups… which is why she is working on changing the status quo for black business owners and black women entrepreneurs in particular.

By definition, Karla is a Bold Type: More than 6 of 10 U.S. businesses are owned by men, and 86% of company owners are white. Karla is on a mission to share her experience and expertise to help black women build their businesses into engines of growth and prosperity that affect structural change.

Such a far-reaching transformation will take many leaders working towards increased equity over time. But as the Chinese proverb goes, “The journey of a thousand miles starts with a single step”. Bold Types like Karla know that it’s the consistent, seemingly small efforts that produce results in the long term.


Keep Moving

The skilled trades have had a rough few years: Baby Boomers retiring at a rate of 10,000 people a day brought a decade-long talent crisis. Supply chain issues left many scrambling to keep up with demand. Lead times were long, projects were understaffed… and then came a global pandemic.

In situations like these, many business leaders would be inclined to proceed with caution. To grit their teeth, hunker down, and hope that things eventually returned to equilibrium. But Deven Paolo knew better. Deven is the owner and President of Solid Form, a custom metal fabrication business in rural Oregon — and he used every new obstacle as an opportunity to learn and pivot. When faced with recruiting challenges, he worked to bridge the gap between education and business (an idea that landed him on the TEDx stage). When the pandemic upended his industry, he completely reinvented his business model. At every turn, he found ways to press forward rather than standing still and accepting the status quo.

Sometimes “pressing forward” actually meant taking steps back. Other times, progress felt more like trial and error than a straight line. But that’s where learning happens. And what Deven (and all Bold Types) knew was that growth, progress, and innovation rarely come from a “wait and see” attitude. In fact, the opposite is usually true: the mark of a successful business is to keep moving.


Stand for Something

Then again, consistently moving forward requires energy. Lots of it. How do you maintain enough perspective to play the long game, or stay motivated enough to keep moving — especially when it feels like the universe is conspiring to make you fail?

Another thing all Bold Type leaders have in common? They’re fueled by their vision of a better future.

For Anna Ready, that future looks like empowering humanity and creativity in an industry known for risk aversion and compliance. Anna is the founder and CEO of Accrew — an outsourced bookkeeping company. Perhaps unsurprisingly, that’s a space known for transactional services and high employee turnover. But Anna was inspired to challenge that industry paradigm and create a culture where people feel free to be themselves, ask questions, and share mistakes.

That commitment to a great employee experience hasn’t been easy — and in fact, at times it’s even had to take priority over the financial or operational needs of the business. But all good values require sacrifice. And what Anna understands is that Bold Type leaders stand for something. Their convictions give them the energy to keep pursuing their path, even through challenges.

Are you a Bold Type?

Being bold in business means taking calculated risks and being willing to try new things. It means not being afraid to fail and learning from your mistakes. It means being proactive and taking action, rather than waiting for opportunities to come to you. What is “bold” isn’t always the most brazen, provocative option: Sometimes it’s bold to turn down an alluring offer, or to stay on your current path when it would be easier to chase a shiny object.

In short, Bold Types are driven to build something bigger than themselves.

Does that sound like you? Join us at the Catalyst Summit on September 7-8, where we’re bringing together visionary leaders of owner-run businesses. You’ll hear from Karla Trotman, Deven Paolo, and Anna Ready, as well as a number of other speakers and panelists making bold moves. But space is limited, so be sure to claim your spot!

Join us for Catalyst 2023!


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