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Entrepreneurs: Choose To Challenge Yourself As A Leader

Dr. Ali Hill is a sociologist, executive advisor, business leader, and the founder of Sound Advice Women.

As part of Women’s History Month in March, the theme of this year’s International Women’s Day (March 8) was #ChooseToChallenge. As entrepreneurs and businesspeople, many of us challenge things daily — the patriarchy, white supremacy, the status quo, the myth of the bimonthly paycheck as safety and security, to name just a few. The urgency behind this sentiment animates our daily professional lives.

Challenging Yourself As A Leader

Yet there is more to this hashtag than a rallying cry to change society, norms or systems of oppression. It also charges us, as leaders, with turning inward and reflecting on what we are doing, how we are doing it and why we started in the first place. 

As we grow our businesses and amass success, it is easy to move away from what brought us to the work in the first place. While we spend hours on our mission, vision and values for our entities, these can get lost in the day-to-day realities of running our ventures.

Self-reflection, for many, becomes a luxury we still feel we can’t afford, regardless of our financial success. We may see the challenges around us and focus on those, rather than doing an internal audit of what we need to challenge within ourselves.

Traveling Your Own Path

As entrepreneurs, we look to forge our own paths. We live by the words of the poet Antonio Machado: “Caminante, no hay camino. Se hace camino al andar” (Traveler, there is no road; you make the road upon traveling). We wear the lack of road map as a badge of honor, skillfully plotting coordinates and designing new ways to access success. 

We pour our energy into making our ideas into realities. The adage “ideas are cheap” rings a cautionary bell in our ears. How would we even begin to challenge what we’re doing when we’re so busy doing it?

In her book, The Moment of Lift: How Empowering Women Changes the World, Melinda Gates asks us, “How do you follow your plan and yet keep listening for new ideas? How can you hold your strategy lightly, so you’ll be able to hear the new idea that blows it up?” Similarly, how do we look inward and challenge ourselves when we are driving toward already-agreed-upon outcomes? How do we stop long enough to know if we are going in a direction that feels meaningful to us?

Four Ways To Challenge Yourself

With the goals of meaningfulness and purpose in mind, here are four ways to challenge yourself as a leader and business owner:

1. Beware of the trap: 'a crown on your head and shackles around your feet.' These are words from Zainab Salbi in her book, Freedom is An Inside Job. When you start your own business, there are services or products you may add that are meant to be temporary — to get you past a certain milestone, bring in customers or help you scale. It happens, sometimes, that instead of those things being ancillary and time-boxed, they somehow become core to your work. Or similarly, you grow your business to the point where you are far removed from the work you loved and instead have a new role that makes you unhappy. Check in with yourself and make sure you like what you see happening in your business. Remember to wear the crown on your head and stay agile. Anything that limits your mobility decreases your power.

2. Center yourself in the narrative. There are many memes and quotes that relate to the idea that “there is no ‘I’ in ‘team.’” As an entrepreneur, there needs to be an "I" in your work, especially when you’re getting started. How are you making sure that you, as the founder, are aligned with the work you and the company are doing? Where is your voice? How is it being heard? Are your mission, vision and values at the forefront of what you are doing? If not, how can you change that and recenter yourself in the narrative?

3. Play your own game. The calculated risks entrepreneurs take are many. Yet, these acts of bravery and vulnerability often morph into a never-ending series of searching for best practices or looking at what others are doing to determine success or failure. It is easy to see how this happens, so it is even more critical to stay vigilant that it doesn’t. You made the decision to go after something that you wanted — make sure you always feel that’s what you’re doing.

4. Define success for yourself. There are so many tropes about what success looks like that it can feel like a radical act to forge your own definitions. Do it anyway. If this is your business, then you are in charge of what success looks like. 

Once we become entrepreneurs, we shed some of the trappings of systems that do not serve us, oppress us, frustrate us or ask us to choose among aspects of our identity. Within these incredible opportunities entrepreneurship gives us, we must remember to self-reflect, course-correct if need be and make sure that we haven’t re-created any of the reasons we took these risks in the first place.

Choose to challenge yourself. We will all benefit from your work.


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