When You Know, You Know


4 Surefire Ways To Know You’re Cut Out For Entrepreneurship. As Told By 7-Year Entrepreneur Erin Woodward Of Nashville, Tennessee

It's never easy to take the leap, and there's always a bit of uncertainty in deciding to do so, but there's nothing like founding a company, working outside of a predictable system, and creating your own path. Deciding if you're cut out for entrepreneurship is very much based on personal intuition, aptitude, ambition, and self-awareness, but there are some patterns, signs, and tendencies that many of us living the self-employed life share in common that helped us align ourselves to leave traditional life & corporate employment behind.

You Tangle With Your Bosses And Structure In General. Hello Insubordination!

I can't tell you how many times I was called insubordinate.  It started in my household as a non-compliant child (sorry mom and dad) and bled into my corporate life.  My all-time favorite occurrence was when my boss pulled me aside for being routinely 5 minutes late for work, explaining that it impacted the team's morale and that I needed to be precisely on time, or else.  I politely replied that if he wanted me to act like everyone else, I would start performing like everyone else, and is that really what he wanted me to do? The stick being, I'd give him the 5 minutes, but my sales numbers would tank because he would be stifling my flexibility. (To this day, having flexibility is what keeps me sane, inspires creativity and high-performance.)  He glared at me, and from that moment forward, he waited for me to mess up, but ironically, I never made him look anything but good to his bosses, and my job performance often carried the entire team for our monthly, collective sales goals. Would I ever be late for a client meeting or high stakes environment, no.  Would I be late for this job, yes, it didn't matter in the slightest given the tasks at hand - that was my point.

Upon my departure from that department, he presented me with an inscribed pocket mirror (that I still have to this day) that says, "You are Looking at Someone Special." Despite being categorically "insubordinate," I was always focused on optimal performance, so while my boss and I had a contentious relationship because I was not a "yes" person and did not fit the exact mold, he just left me alone to do my job, and do it well, and we just never spoke about my insubordination again. Ask yourself, are you insubordinate because you know you're delivering results, and you're doing things with your own methodology? Do you struggle with structure and know you have a better way of getting from point A to point B? These could be signs you'd be more fulfilled working for yourself.

You Beta Tested A Concept And It Didn't Implode. 

The closest I ever came to entrepreneurship before I was an actual entrepreneur, was a hybrid idea I cooked up when I wanted to move cross country to be with a boy that ultimately worked out because it didn't work out.  I approached my current company's parent company and pitched them on a role that I dreamt up and wanted to pioneer.  At first, they said no.  I kept going back to key decision-makers and speaking to more people until they saw the value in what I was proposing.  I knew I wanted to live in Chicago and/or NYC, I wanted President in my title, I wanted six figures and I wanted to travel, SO, I came up with a business plan to grow assets by representing portfolio managers.  My vision for this new role meant getting paid to travel the US with complete autonomy, meeting with Brokers, Broker-Dealers, and Distribution Partners to raise AUM.  Without an MBA or JD, literally, the only thing I had going for me was the fact that I knew 400 people I could "sell" to, had a solid reputation, was very persistent, and I'd like to think, half charming.  After 3 months, two face-to-face meetings between Denver and Chicago, a video conference interview, and 7 hours of back-and-forth negotiation, I landed the gig.  I wrote my own job description, and moved to Chicago.

This is where my love for fine dining was stirred and, in this role, I met and married the love of my life, not the boy I had moved for.   I'll never forget my final sales pitch when attempting to create this role!  I was having lunch with the final decision-maker, and my closing statement was, "Mr. Boles, I have to imagine that at some point in your career, you were sitting where I am today, and someone took a chance on you.  I'm asking you to take that same chance on me."  Staring at him in silence, I got the job.  Ask yourself, do you have a vision, idea, or business plan that has yet to be tried, and you're ready to give it a go? The corporate environment is a safe environment, I had the safety of the company backing me. My life savings wasn't at risk, but I learned a lot about my aptitude and wherewithal when they gave me the opportunity, proving to myself I was ready for entrepreneurship, and I was just getting warmed up with this first go-round.

You Gravitate to Hard Things, Like a Seemingly Impossible Challenge.

Oh, you mean no one else wants to do this, or is capable of doing it?  Raise  hand - I'll do it.  Oh, this hasn't been tried before. Raise hand - I'll do it.  Public speaking? Sounds Energizing.  Long hours? When do I start? Faraway places? I love unchartered territory. Uncertainty? Yes please, where do I sign? Performance metrics and pay is based entirely upon my own efforts?  Sounds awesome! Ask yourself all of these questions, what's your honest, gut response. Level with your authentic self.  If none of them scare you away, then perhaps you're ready to take a closer look at cutting the umbilical cord.  If some of them sound scary, warning-heeded, you're not going to love entrepreneurship.

You Reject the Typical.

I have never made any decision leading with, "but, will they like me?" It just never crosses my mind.  I know I'll always do the right thing, I'm okay with self-sacrifice in the face of doing the hard thing, and often, both success and happiness require unpopular decision making. Aside from that, there's the typical path that involves college, acquiring massive debt, securing a 9-5 to pay off said debt, securing a life partner, a house purchase, acquiring more debt, kids, acquiring more debt, getting old & death - blah - and that path just wasn't for me.  I've always valued freedom and have very little desire to be like my neighbors, friends, or family. I cherish them all for who they are, I am just not wired that way.  In a world of mimetic desire, you're either creating the desire (you have what others want) or you're chasing the desire (you want what others have). I desire what I create, and I create what I desire, in a closed system and endless loop. I just wanted to be left alone to create and express myself in each unique way as the moments strike with only myself to worry about, and that's impossible with the cookie-cutter lifestyle. I don't value possessions or status, but I do value luxury, quality, creativity, and freedom.  As I went along my life's journey, I realized I'm happy with my life as it is with just my husband, Goldendoodle, and freedom at the center of my universe.  I don't want to throw my Zen out of homeostasis, so I've opted out of the traditional model.  It's also allowed me to move about freely and not worry if I failed at any stages of my business ventures, I wouldn't be leaving my family destitute.  So, the last basic aspect to check in with yourself on is what's MOST appealing to you in everyday life?  Do you see yourself married with kids/family being the focal point of your lifestyle?  Or do you see yourself as adventurous, unable to "settle' for the typical journey?  The typical journey is beautiful and magical in and of itself, it's just not for me! There's always an opportunity later in life to start a family, if and when priorities change, and/or entrepreneurial aspirations are stable and fulfilled.

Learn more about Erin Woodward and her entrepreneurial journey on her personal website and social media.

Copyright © 2024 Erin Woodward. All Rights Reserved. | Fotografie by Catch Themes
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