Becoming Comfortable In Your Own Skin

As we get older, most of us become more comfortable with who we are as people.  We begin to understand our own strengths and weaknesses better and we’re more accepting of those limitations.  In essence, we become more comfortable in our own skin.

I’ve always been a pretty confident individual, so when you combine that with the exuberance of youth, a bit of naivety, stubbornness and ambition it could make me something of a force of nature when I was younger.  I simply didn’t take “no” for an answer and I just didn’t pay attention to commonly held opinions.

I was able to convince the CEO, CFO and COO of a company making $14B per year in Construction, Mining and Engineering to give me $10m to start a new technology business and another $1m to buy a software company from a Telco.  Then I convinced them to give me $6m more so I could acquire an IT security company as well.

I didn’t listen when people told me that technology companies selling to “enterprise” customers needed to have sales teams.  That didn’t resonate with me because I knew it was wrong – having guys taking people to lunch and haggling down our prices or giving away free professional services time just seemed stupid to me.  I started looking at marketing and discovered the world of direct response marketing.

I then applied those principles to the software business, turned it into a SaaS business and decided to market directly to customers rather than IT people who didn’t understand what the system did or how it applied to their business.  The IT Directors and CIOs all told me they would use competitor systems or “write their own”.  Youthful arrogance kicked in and I knew our software was better and that they weren’t smart enough to write their own otherwise they’d already had done it.

That business exploded.  In three years we went from 25,000 “users” to 75,000 monthly paid subscriber accounts.  Our email list was massive and we’d built a whole portion of revenue from affiliate marketing that would never have been possible if we’d have stuck to the traditional sales model.  Revenue when from $1.5m to $11m per year during that time.

But here’s the thing, the only reason I was able to drive that outcome was that ultimately, I was uncomfortable with myself.  I didn’t understand my own limitations and the volatility of the outcomes didn’t register with me – I was too arrogant to think I might not succeed with my vision.

Flip to today and I’m far more relaxed, considerably less ambitious and my confidence today comes from a place of experience and thoughtfulness rather than hubris and arrogance.

All up, despite having far less lofty desires for myself and my business, I’m a much better entrepreneur.  I routinely make better decisions, I take far less risk and my plans are much more deeply thought out.

I have nothing to prove now, so my desire to be successful is purely internal.

What that translates into is the ability to know when something is working and when something is patently broken.  At 42 years of age with 20 years of business experience under my belt, I can look at something, see that it’s not working and occasionally appreciate that it’s not worth the effort to fix.  When I was 30, I would have simply “decided” to fix it and make it right – that potentially would have led me down a path where I wasted time and resources pointlessly.

I think it’s overly simplistic to call this “experience” or “wisdom”.  I genuinely believe that it comes from being more comfortable within yourself, having a certain level of self-awareness and knowing that you don’t need to hit a home run on every pitch every time you step up the plate.  I’m patient and thoughtful because I’m aware of who I am, what my limitations are and how best to channel my strengths.

That’s the key in becoming a better entrepreneur at the end of the day – you need to be able to understand yourself, what you’re good at, what you need help with and feeling confident enough in yourself to accept failure sometimes.  And when you do get those setbacks, you’re wise and experienced enough to know that those failures are learning experiences for the next time you face them.

Basically, I believe that when you’re comfortable with who you are, then your business will flourish because of that.

Leave a Comment