Why feeling comfortable should make you feel uncomfortable.

I am always looking for nuggets of wisdom. And because I am always looking, unlike Bono, I often find what I am looking for. The latest gem arrived yesterday from Robert Kiyosaki, the famed investor and author of Rich Dad. Poor Dad. Kiyosaki is an active tweeter, dropping 140-character bread crumbs of wisdom throughout each day.

Here is the tweet that has me all atwitter right now:

The biggest trap, the biggest dungeon in life isn’t laziness or bad luck, it’s comfort.  -Robert Kiyosaki 

The Human Trap

I know exactly what Kiyosaki is talking about. And he nailed the big ole human trap. If I was trying to catch me a feast of humans, I would not set out an oversized mousetrap baited with oversized cheese, or a giant ant trap baited with a giant picnic basket.

Instead, I would set up a steady 9-to-5 job in middle management, with competitive benefits, no night or weekend work, no travel, a swell group of co-workers, an easy commute and decent pay. And my trap would suck in humans like a new and improved black hole designed by James Dyson.

Dissecting The Trap

Comfort is a trap. It slowly and silently pacifies you. It lulls you into a false sense of security. Comfort takes your ambition, hands you back mediocrity, and makes you feel like you got fair value in the exchange. Comfort smothers dreams, dismantles goals and leads to the motherlode of regret that so many people unearth in their last chapters.

Staying Uncomfortable

Most people are looking  to make a comfortable living. But that is my greatest career fear. Because it would mean that my career would be good, but never great. It wouldn’t be memorable or laudable or history making. It wouldn’t create a legacy or generational wealth. But most importantly it wouldn’t allow me to accomplish my personal mission and live into my personal legend. #TheAlchemist

A Quick Recap

I spent the first 19 years of my career working as an employee. I earned fancy titles that included words like Executive, Chief and President. Those roles generated internal clout and an enviable salary that most would be thrilled to have. And most people would never give it up.

The Grand Illusion

My past jobs offered a great deal of perceived comfort. But that type of comfort is an illusion. It tricks more people than David Copperfield (Vegas not Dickens). Jobs are not steady or guaranteed. They only appear steady because people want to believe they are.

Entrepreneurship felt like the path to the endgame comfort I was looking for. Because the comfort I want comes from having control over my time, which is our only un-renewable resource. So in 2016 I launched my own advertising and idea agency, The Weaponry.

Even More Dangerous

However, entrepreneurship does not make you deaf to the siren song of comfort. Worse, a sense of comfort is far more dangerous to entrepreneurs than it is to employees. Entrepreneurship requires you to always feel unsatisfied, incomplete and scrambling to generate the next phase of growth that keeps your machine humming.

I stay uncomfortable by committing to goals that are very hard to achieve. Those unattained goals provide a constant feeling of discomfort. Of failure. And of motivation that drives me forward. I try to keep that discomfort front and center. Because it prevents me from falling into the big trap that Robert Kiyosaki warned the Twitterverse about yesterday.

Key Takeaway

Comfort is the enemy of high achievement. It makes you feel as if good enough is good enough. Comfort forces you to pawn your hopes and dreams. It makes you lay down your ambition and stop fighting. But don’t. Don’t give into comfort. Keep your eyes fixed on your original dream. And make it come true. Because that is the only way to guarantee you will feel comfortable with the way your story ends.

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The Perfect Agency Project

I am an advertising enthusiast.  Well, technically I’m an advertising professional since advertising has been my primary source of income for almost two decades.  But I call myself an enthusiast because I’m enthusiastic about the industry and energized by its ever-increasing potential to help businesses grow.

I’ve had a pretty decent career so far.  I started as a copywriter.  And at 37 years old I became the Chief Creative Officer of a 275 person ad agency with four offices.  Recently I was asked what challenge I want to take on next.  The answer is simple.  I want to spend the rest of my advertising career creating the perfect agency.  No big deal, right?  Just perfection.

To be successful I’ll need two things.  First, a vision of what the perfect agency looks like.  And second, the drive and determination to narrow the gap between the idealized vision and where we stand at the end of each business day. I believe that the ideal can be achieved at any agency, as long as the team is committed to continuously absorbing and implementing the best ideas.  I expect this to be a stimulating journey.  And I’m sure feathers will be ruffled.  On this quest, I also expect to have a lot of fun, to create a lot of interesting work, to develop deep relationships with my clients and coworkers, and to make a lot of money for the agency and our clients.

I’ll share my learnings, experiences, challenges, conversations and successes along the way.  And I want to hear from you.  So I am calling on the experts, the newbies, the peanut gallery, and even the clients’ wives, and husbands. I want to hear as many perspectives as possible.  Because if I’m to help create the perfect agency it’s going to have to work for everyone, employees and clients alike.  Oh, and by the way, in the perfect agency we might not call people employees or clients. Oh snap! That’s called foreshadowing.