9 Lessons Being an Entrepreneur Has Taught Me about Leadership

Calling myself an entrepreneur has challenged my identity and my beliefs about who an entrepreneur is.  In fact, just spelling the word is challenging! As I’ve done the work of building my company, designing my brand, and creating content; claiming the title has been fun and liberating. While I’m still new to the world of entrepreneurship, I think I’m pretty good at it. I love the people I am meeting the work I am doing and am more than happy to work a late night or on the weekend.

Recently I had an a-ha. The lessons I’ve learned and am still learning as an entrepreneur make me a better leader and manager. I wish I would have had the benefit of this experience earlier in my career. I would have been a more effective leader, and happier.

In the last 10 years, the landscape of business has seen large shifts. I remember when I didn’t want to live more than 10 minutes from a Blockbuster. Now I have Netflix on all of my devices. Gone are the lazy Sunday afternoons walking through the aisles of Borders picking up random books because their cover looked interesting. As new technology and possibilities arrive, paired with our demand for convenience, companies must be a step ahead. They must know their customer and be willing to pivot their mission to respond. As an entrepreneur, I realize this change is being led by other entrepreneurs willing to take risks and try something new.

This change is accelerating, and companies that want to stay in business must have leaders who can help the company compete and be ahead of the change curve. Working in leadership development, I understood that we needed leaders that could work in an ambiguous, complex and uncertain world. Now I get it! As an entrepreneur, I live it every day.

I’ve written before that to be successful, each leader will need to develop themselves in 5 skill sets: inner game, leadership, management, domain expertise, and entrepreneurship. Today I want to go in depth about the 9 lessons being an entrepreneur has taught me. The lessons I wish I would have gotten not just understood as a leader while in my corporate positions.

Step 1- Start this very moment to think of yourself as an entrepreneur, because you are. As defined by Merriam Webster an entrepreneur is "one who organizes, manages, and assumes the risks of a business or enterprise". It comes from Old French, entreprendre to undertake. You are an entrepreneur. You manage and assume the risk for your life, your career, and your team. You must act as your own President and the leader of your own cause. As an entrepreneur, you step into a direct role of ownership, responsibility, and power.

Step 2- Learn from the 9 lessons being an entrepreneur has taught me about leadership.

#1- It's up to you!

As an entrepreneur, I am 100% responsible. The buck stops with me! I don't have a job, a career, or work. I work. I have a company and direct responsibility for every decision I make. While in my corporate roles, I longed to feel like I had an impact and to know how I was contributing at work. What I realize now is I was waiting. I was waiting to be told how I should add value. Waiting to be given permission on the problems I could solve. If I did it again, I would approach my job as if I was the President. I’d assume more risk and come forward with more ideas. Taking steps every day to develop my team, myself and deliver results and real change. I wouldn’t wait for permission and guidance. I’d advocate for an idea and lead. This is what your manager and companies are looking for today. Your manager doesn’t have the answers, they don’t know what you know. They need your perspective and your ideas. It is up to you.

#2- You are the Vision & Mission

All the entrepreneurs I’ve met, including myself, have all created business' based on their passion and a problem they want to solve. The idea is based on who they are and how they see the world. It becomes the foundation of the company and its vision (the dream) and mission (how the dream will be accomplished). As founders, they are a walking billboard for their vision. Bringing it to life, for everyone they meet.

As we interview and decide on an offer there is a checklist that we are looking for: right role, culture, right manager, pay, perks, location, growth opportunities, flexibility and whatever else is important to our lifestyle. One of those checks is usually a general interest in the company and its product. But, how often are you truly passionate about the vision and mission of the company you are working for? Could you be a walking billboard? If I did it again, I’d place more importance on working for a company that matched my personal vision and had roles that allowed my mission to be lived at least 80% of the time. When there is greater alignment I believe it's easier to be engaged, excited and motivated; especially during the tough times.

#3 - Lead & Live the Story

Lead and live the story is to put into action the alignment of vision and mission. As an entrepreneur, others don't know and may not yet have the passion you do for your product. As the leader, your role becomes setting the example and lighting the fire of passion for your team, customers, and partners of what is possible if the mission is accomplished. Through our presence and decisions, we create a culture and a story that become the rhythm for all that is to come. If I did it again, I’d lead with the story and let my team create the right strategy and goals. Once you are aligned with the vision and mission, our role is to keep telling the story. Over and over, encouraging and empowering our team to achieve the mission.

#4- Know your Customer

While at PayPal & eBay one of our values was “Be the Customer”. I understood that if I don’t use our product how would I understand the customer's experience and perception of the company. As part of our work, leaders could watch customers in labs, go to on-site visits with customers, or spend time listening to customer calls. I used PayPal as much as I could and sold things here and there on eBay.

As an entrepreneur, your business depends on knowing your customer. Not just knowing, but being. Using their language, understanding their lives, their problems, and their joys. I spend a lot of my time listening to leaders. I wonder what problems they are facing and what challenges they have overcome. I pay close attention to the words they use. People want to feel like you get them, that you understand them. They want to resonate with your vision and mission. If you do it right, you never have to market at all because your customers do the marketing for you.

Early in my career, I wanted to prove how intelligent and unique I was. When summarizing something, I’d like to add my own poetic flair and restate it better. There is a time and place for that, but as an entrepreneur, I’ve realized it’s not about me. It’s about my customer.  Words make a difference. Some people want to be confident, some courageous, some brave, some bold, and some fierce.

If I did it again, I'd put my focus on others more and see everyone as my customer. My team, my manager, my peers, and my customers. I'd want to know more about them and their problems, to make them successful in their work. I'd be curious about them, their work and how my team impacted their lives.

#5- Know your Market

As an entrepreneur, I want to bring my vision to life through my mission and strategy. Part of this work includes understanding the ecosystem I’m working in. Beyond thinking about my customers, I’m curious about my competitors, new approaches to leadership development and coaching, regulation of the industry, and what others are trying that worked and failed. If I did it again, I would have taken time to be curious about changes in my industry and new innovations that could impact my team. I know that knowledge would have given me an advantage at work and more thoughtful opinions on solutions to the problems we were facing.

#6- Always be Learning

As an entrepreneur starts their business, they do it all. I now spend time on business development, marketing, operations, accounting and everything else that comes with running the business. I personally like to plan time for working on my business and working in the business. Since becoming an entrepreneur I've learned about social media, customer engagement, marketing, SEO, CRM's, contracts and so much more. I now know so much more and have a greater appreciation for running a business and not just the product development life cycle and HR processes.

As you step into the role of entrepreneur, I encourage you to be curious about how your company works. Step outside of your organization and learn about a new area. Having a broader understanding of your company will help you be a better leader who thinks systemically and not just locally. If I did it again, I'd also continue some of the learning practices I have now, like listening to podcasts, reading books, listening to books, and being genuinely curious about other areas of business. You never know what you may learn that could spark a new idea.

#7- You Can Figure it Out

At the end of the day, the buck stops with me. I make all the decisions. There is no one to go to for direction and guidance. Yet, I don’t know it all. Being an entrepreneur has helped me get over the I have to know it all, do it all, and be perfect at it all mindset. I actively invest in mentorship, coaching, and programs to learn what I don’t know. However, no one will know what’s better for my company than me.

Not knowing, being scared, or stuck; it’s all up to me. A key belief and mantra- I can figure it out. I will figure it out. It's an encouragement that makes me more creative, helps me take a new perspective or take a risk when I want to stay safe. As you step into the role of entrepreneur, try on the same attitude. What if the buck stopped with you? What risks would you try? Who would you ask for help that you wouldn’t think of? Having a figure it out mindset sets a tone of adventure and I can do it attitude. It’s empowering.

#8- Define Success

Growing up success is defined for us. We went to school, studied, took tests and got grades. When we are hired into a role we are hired with a title and a pay level. We set goals and accomplish them. Our pay, bonus, stock, and benefits are paid for our work. Yet our goal is to grow and contribute more; hopefully, in return, we get to work on cooler projects, get promoted, and more financial incentive. Success is set for us.

As an entrepreneur, there is no title, pay, stock, levels, or bonuses. There are new metrics to follow: revenue, followers, intro phone calls, and deals; just to name a few. Still, these aren’t the metrics of success. As an entrepreneur, look at the entirety of your life and decide what success will be. If you were on your death bed looking back at your life how do you want to measure and take stock of your life? That is success and what you want to work for, everything else is someone else's expectation and it's time to let it go. If I did it again, I wouldn't be as focused on my rating, bonus level and if I was going to get promoted. I'd have a new measurement of success that looked at the whole of my life and make decisions according to that.

#9- Rest

I’ll admit I can be a workaholic. Early in my career it was driven by the feeling of always being behind, then as my roles got larger it became about proving myself, and now as an entrepreneur, it’s about passion and wanting to provide more for my clients. Working at a corporate job, I always had a vacation plan, sick days and corporate holidays. As an entrepreneur, there is only me, my goals and 168 hours a week. When I get sick there is no backup plan. I am my company and my brand. This reality has given me the motivation to take better care of myself. After big events, I schedule downtime for myself. During the day, I schedule breaks and get out of my chair. I do my best to eat well and get enough sleep. I simply can’t afford to burn out.

As an entrepreneur, you can’t afford to burn out either. You can't offer your best ideas, be more creative, and present with your team when you aren't rested. You’ll be more resilient, flexible and able to flow with the punches of the day when you invest in your own wellness. Remember, you only have 168 hours a week and so much energy. Be purposeful with it and it's amazing what you can accomplish.

If I did it again, I'd set better boundaries around my time in the evenings and on the weekend. I'd take every Friday to plan the next week. I'd look ahead to block out time for important strategic work and thinking. I'd arrange my schedule to focus on creative and strategic work in the morning, leaving the smaller stuff for the 3pm hump. I would do what I needed to show up and be present, ready for the ambiguity that work brings.


    About the Author

    Kim-Elisha Proctor is an Executive Coach, teacher, and writer. For over 15 years, she has worked with companies at all stages of growth and understands the complexity of organizations and leadership that is needed for success. Whether one-on-one coaching, with groups or delivering leadership development programs, her passion is the same: to support leaders to enhance their performance, impact, purpose & well-being to create communities they long to belong to.

    Kim-ElishaAgency, Lead Smarter, Personal Musings