December 14, 2022

Pausing From Entrepreneuring to Reflect on Entrepreneuring

Entrepreneurship | Leadership | Personal Growth and Development | Branding
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It’s National Entrepreneur’s Day 2022. I always love to celebrate a day celebrating entrepreneurship. 

This is an update to a piece I wrote for this day back in 2019. Returning to the original piece showed me that the adversity and upheaval of the past three years strengthened my love for entrepreneurship. Today, my thoughts on entrepreneurship are more deeply held, and my work with entrepreneur clients and collaborators inspires and fulfills me at higher level than ever before. 

Entrepreneurs create something out of nothing other than our hearts and minds and hands. 

Entrepreneurs answer a calling that no one can hear or see or touch, and bring it real.

Every brand and business was born in the heart of a regular everyday person who musters a remarkable courage to bring it to life.

Entrepreneurs are master manifesters and social shape shifters. Every entrepreneur in my circle envisions a world that where equity, justice, freedom, and healing have all the space they need to thrive. Together we are creating a force in our communities and in the economy that powers that collective vision. 

I’ve learned from the stories of many entrepreneurs and my own that before we land in the moment we say “yes” to entrepreneurship, every one of us has to say yes to reckoning and rumbling with forces in and around us to fire up our desires and claim our place here. 

My essay provides musings and tips that I hope support anyone who is hearing the knock of their inner entrepreneur and really wants to invite it in, but doesn’t know where to start. I got you. 


On November 19, 2019, my business right-hand Jes told me that it was National Entrepreneur Day. I gave that news a quick “Awesome. I love celebrating entrepreneurs! Yay us!” and then got back to the work of entrepreneur-ing.

Who picked such a busy time for National Entrepreneur Day anyway? I mean come on — small businesses everywhere are in full hustle mode right now. At Asana Consulting, we’re wrapping up our 2022 work, reflecting on this past year, setting our 2023 business vision and plans, and queuing up the first exciting new projects of the new year. Then in mid-December we will switch the channel to Holiday Hiatus mode for some well-deserved rest and play so we can enter 2023 rejuvenated and ready to rumble.

To celebrate National Entrepreneur Day 2022, I’m sharing six musings — one for every year of this entrepreneurial adventure called Asana Consulting plus one more for good luck— on what being an entrepreneur means to me today.

#1

Being an entrepreneur is at the heart of who I am. I am wired for it. I’m a dreamer and a doer in equal measures. My mind moves fast and loves to churn out ideas about innovative products and services that can make money and drive social impact (which makes me what is called a social entrepreneur). I’m spirited and passionate and creative. I’m adventurous — I tackle challenges and I am willing to take risks. I’m easily bored and I’m allergic to monotonous routine. I’m hard-charging and stubborn (or tenacious as my mom says) and independent. My insatiable drive to continuously learn and improve in my work powers an obsessive love for my library of books, articles, websites and podcasts by and for entrepreneurs. I am competitive and driven, like a typical Taurus. I see problems as opportunities and welcome complexity and collaboration. I’m the oldest sister of four kids who will probably tell you that I like to be the boss.

#2

As clear and obvious as my natural orientation to entrepreneurship is to me today, getting to the point of knowing this and saying yes to it took decades of self-discovery and self-reckoning. I started my first business — Nancy’s Painted Rocks — when I was five. I turned rocks from around my house into painted art that generated money for me to make my first-ever charitable donation through my elementary school. Many entrepreneurial endeavors came and went in the ensuing years, but I didn’t give them my full focus and intention for a whole host of reasons until I brought Asana Consulting to life.

#3

Five years and eight months ago I stepped into this identity. That was when I resigned from my VP-level job and decided to focus all my professional and creative energy on building my own business. This was an intentional and radical shift in how I invested my professional energy, going to 100% investment in building other people’s businesses and manifesting other people’s missions to 100% investing in mine. There wasn’t a magical day when I was struck with the epiphany that I was born to be an entrepreneur. It was a slow, mostly imperceptible process until an unforeseen combination of challenging moments and experiences in 2013 gave me a new way of seeing what had been in front of me all along. I embraced what I saw, because the alternative was way scarier. Still, I had a ton of fear and some vocal doubters. I was warned. I was given an explanation.

Being an entrepreneur isn’t an act of bravery for people who are naturally entrepreneurial, it’s just a way of making a living that suits us…Living and working in a way that is authentic to you is the act of bravery. It takes chutzpah and courage, and those are available to everyone of us.

#4

If you ever have a moment like this when your inner entrepreneur starts loudly knocking on your door, I highly recommend saying “Hello darling/gorgeous/handsome/crazy beloved. Come on in.” Do some honest examination and a lot of research about whether you are truly ready and wired for the reality of being an entrepreneur. Say hello to all those fears, and welcome them to the party, too. Then the party is over and it’s time to decide: is this wild, wonderful, wacky path a yes for you? If it is, make it a full, juicy YES. Say it, dance it, jump it, shout it. Do whatever you need to do to claim it wholeheartedly so you remember this moment. Then, start working it. Create your brand. Build your team. Find your tribe. And, if entrepreneurship turns out to be a No for you, congratulations on being honest with yourself (and your steady paychecks ahead!). Life is too short to not be who you are. If you want help crystallizing your vocational mission, set a personal retreat day that includes reading Parker Palmer’s gem of a book Let Your Life Speak: Listening for the Voice of Vocation.

Life is too short to not be who you are.

#5

One of the biggest game-changers in my career was trading in the “What is wrong with me? Why can’t I be like everyone else?” mindset for the “What are my strengths and what are the gifts I am here to share with the world?” mindset. For the first two decades of my career, my work happened in nonprofits and government agencies where I was an employee. I did a strange dance of working as an employee in positions leading start-up projects in predominantly large and bureaucratic organizations. My colleagues and mentors were smart, good people and I cherished our relationships. I loved the work — it was intense, mission-driven, collaborative, challenging, strategic, and creative. It played to many of my strengths beautifully, and I was good at it. But every time the start-up phase of one of my projects ended (sometime between the 18-month to 2-year mark), I landed back at square one. My employers didn’t have more projects at assign me to, only management positions and career advancement paths I didn’t want. It started to feel like “Groundhog Day”: the project I’d built and led would move into successful long-term implementation and I’d set off job searching. Again. And again… and again.

I began to think was on the wrong planet again (this was an actual recurring theme for me from childhood — I made a plate in 1979 showing myself stepping off a spaceship from Mars, antennae and all). I assumed something was wrong with me because I had to keep leaving jobs to find professional satisfaction. People told me to stop changing jobs because it would look bad on my resume, but I didn’t buy that (plus, as I’ve already explained, I don’t give up easily). I held strong to the belief that somehow I could find my way to a professional path that didn’t involve a continual job search or require me to take jobs I didn’t want. These were fantastic jobs for someone, but not for me: I was a free agent being offered positions that I knew wouldn’t sustain me in organizations filled with employees whose primary career goal was to minimize job changes, if not stay at their current jobs until their retirement.

A career coaching relationship in 2010 introduced me to the idea that examining what I loved about my work would illuminate my unique strengths. Sometime after that, I found the Strengthsfinder assessment and gained valuable new ways of understanding my strengths. Suddenly, my resume made perfect freaking sense! I started Asana Consulting by using my strengths as assets and guideposts. Now this is the job I’ve had the longest. Understanding the power of embracing and centering people’s strengths – both mine and others’ – continues to help me immensely. Today my business operates as a company of one connected to a high-performing team of talented experts and colleagues who are all fellow entrepreneurs. It’s common to hear there are only two ways to be self-employed: freelance or build a business with employees. Neither felt right for me. When I learned about the company of one model and that my top three strengths are Connectedness, Strategic, and Adaptability and stayed true my love of doing work that is collaborative, innovative, and builds community, the next steps for my business were crystal clear.

#6

Being an entrepreneur isn’t for everyone, but being brave is. When I started Asana Consulting, a surprising number of people told me, “I’m not brave enough to start a business.” Being an entrepreneur isn’t an act of bravery for people who are naturally entrepreneurial, it’s just a way of making a living that suits us. Hawks aren’t brave for sitting at the tippy-top of the tallest trees and soaring across the sky, they’re just being hawks! Living and working in a way that is authentic to you is the act of bravery. It takes chutzpah and courage, and those are available to everyone of us.

Here in the season of reflection and thankfulness, I’ll wrap this up with my Entrepreneur Gratitude list:

  • I am grateful for Asana Consulting’s clients, collaborators, supporters, advisors, and friends. Thank you, Asana Consulting tribe, for all you’re doing to make my entrepreneurial dreams a reality and to cheer us on in our work with brave, authentic, and inspiring leaders, organizations, and businesses.
  • I am grateful for my team: the brilliant squad that powers this business in every way with their skills and talents. You make my “company of one, team of many” business model sing! Thank goodness nothing good happens alone — I wouldn’t want to do any of this without you.
  • I am grateful for the intermittent “fraudy feelings” as the bosses at Being Boss say that surface and the unprecedented challenges that have come across my entrepreneurial path every year. They’ve gotten my attention and given me valuable opportunities to pause, step back, evaluate, and reset with new awareness and new insights for the road ahead. I’ve also learned some hard but very valuable lessons about trusting my gut.
  • I am grateful for the opportunity to continue on this path, and the knowledge that it’s the right one for me today.

#7

Know this: there’s magic in this process ✨✨✨✨ Look for it, welcome it in, and co-create with it. If you’re looking for some superpowered inspiration along these lines, read (and re-read!) Elizabeth Gilbert’s Big Magic: Creative Living Beyond Fear

Adapted from the originally essay published November 27, 2019 on Medium.

Nancy Lord
Founder & CEO

Nancy is a Baltimore native who came to communications and marketing through her work in public health. In 2014 she took an entrepreneurial leap of faith to start Asana Consulting and she found her wings.

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