5 Leadership Lessons I Learned From Entrepreneurship

Updated: Mar 5



Leaving Corporate America to start my own business was something I certainly said I would never, and could never do. (God likes to prove me wrong often, does that happen to you, too?!) I guess I thought I didn't have some sort of special entrepreneurship gene. Entrepreneurship isn't a leap for everyone, but I learned some lessons in my first year that, quite frankly, I wish I would have known in corporate America. I probably would have been a lot happier and more successful. My teams would have enjoyed elevated confidence and results, too.


What I learned quickly out on my own was that the steadiness of a paycheck every two weeks hid many bad habits that quickly became exposed when I had only myself to rely on to earn a living.


Here are five lessons a full year of entrepreneurship taught me.


Embrace Uncertainty.

I wrote the following mantra on a post-it and it sat on my computer for months. “Accept the fact you might have no idea what you’re doing. And that's okay.” My clients often stress because they think they need a perfect plan or perfect results. We will often spin in analysis paralysis and wait until we have perfect clarity on the next step. What I learned going out on my own, was getting super comfortable accepting the fact that uncertainty was my certainty. I had no idea how my decisions would pan out. There was no “right path.”


Grasping for a perfect path taught me that I had to stop just relying on my intellect and I had to tap into what I often call my “other ways of knowing.” Instead of searching for the proof my mind thought it needed, I had to learn to trust my gut with every decision. I asked myself some questions. Does this align: with my values? With what I'm trying to create? In my body - does this feel of peace or chaos? Learning how to use our body as a compass is a valuable tool and I teach it to my clients, too.


Fail Fast.

“Kill your darlings.” This is actually writing advice from Stephen King, but we have darlings at work, too. Darlings are the projects, passions or initiatives we are certain will work because we’ve fallen in love with bringing them to fruition. I definitely had them while in Corporate America. But when you're running your own business, I've learned you have to kill your darlings – fast. Holding on to ideas I loved, but my clients didn’t, was expensive.


I was so frustrated when things I dreamed up didn’t go as planned, but instead of losing my confidence, it inspired me to get curious. I learned to have the humility and courage to kill off the things I cherished I could pivot quickly in support of the things that worked in reality. Failing fast is a skill. A great book to help reframe your mindset about testing and refining new ideas for learning over perfection is the Lean Startup. Have the courage to set aside the need to be right so you can be successful.


Check Your Expensive Mindsets.

When I started my business, I planned my marketing expenses, my operational expenses and startup costs. What I didn't factor in was how expensive my mindset would be - specifically stalling. I was so scared to put some ideas out there for fear of what people would think. I learned quickly that every day I stalled was an expense to revenue because it delayed opportunities for connections. A bi-weekly salary hid this expense.

I think about how often I stalled in corporate America out of fear wanting to look perfect. But to earn a paycheck when you’re on your own, I quickly reframed to striving for learning and not perfection. I had to learn how to break things into small, brave steps so that I could take action. Today.


I had to reframe my mindset from, “what will people think” to “I have something helpful and people should know about it.” Had I thought that way in Corporate, I think I would have been a stronger advocate about communicating my ideas. This means I have to consistency find ways to advocate and ask.


Know Yourself.

This is the hardest since we live in a time where it’s so easy to have comparison at our fingertips via our smartphone and social media apps. It’s tempting to try and copy what’s made other people successful. This is basically just strategy convergence – where we all copy each other and go after the same thing in the same way and lose what makes us unique.


So, getting very clear about my strengths, core values, personality preferences and zones of genius will serve me better than knowing how to run all the processes perfectly. Knowing myself is better than knowing my business niche. Knowing myself is better than knowing what my future holds.


When I know myself and my values, I can make decisions that align with my why, my purpose, and what I've been called to do. Recent Harvard research shows that it pays to be yourself. There's something deeply attractive about somebody showing up as their true self. I'm still trying to figure that out, but only every day I'm thinking, how can I know myself better? How can I show up for myself? How can I advocate on behalf of my values and live my purpose and do it in a way that I hope helps others?


Consistency Over Time.

Showing up for yourself sometimes is a very uneventful thing. When you constantly are putting yourself out there, whether you’re in the office or on social media, sometimes it feels like nobody's listening. I don't know about you, but I feel like indifference is harder than attention, whether it's positive or negative. It takes courage to keep advocating even when you think nobody cares or is listening. To show how silly our ego works to keep us playing small, I remember thinking that when I started my own business, I would have this big exposure problem and it would activate my “what will everyone think” monster.


But exposure isn’t our real problem. Our problem is obscurity. This world is so noisy, whether we're working for corporate or working for ourselves, it's a noisy place. People aren't thinking of us. That's the problem. Consistency isn’t sexy, but it does work when advocating for your ideas and your cause is important to you.


Whether you're running your own business or in corporate America, how can you can be consistent? How are you honoring your values? How can you focus on ideas that are truly working?


I hope that you have the courage to take some small, brave steps through ambiguity and do something amazing.


Calling all women leaders! Are you ready to define your leadership brand and advance with confidence and creativity? My Rise Confidently Leadership Masterclass begins March 24! Learn more and grab your spot for this unique development experience!


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© 2020 by Kelli Thompson