Do You Have a Love-Hate Relationship with Freedom?

freedom

I certainly do.

In one sense I crave freedom… it’s what this blog was born out of. Freedom from the traditional 9 to 5 job, from a traditional life, from the (perceived) monotony of the same daily routine for months, years… decades.

Alternately, I crave safety. It’s biological. You probably crave it too. Safety, companionship, love, a family unit, community.

There is a continual tug of war going on inside of my head. Which do I prize more: freedom or the human need for closeness, for one’s tribe, and for roots?

The answer is: I don’t know.

Both…?

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Escape the San Francisco “Summer” and Roam the World!

SF FogIf you can see me over that mountain of scarves you piled on to fight off San Francisco’s infamous summer chill, raise your hand… and if you can lift your arm with those three sweaters on, even better.

Listen… I know that summer in SF can be “cool” and not just because the thermostat is reading in the low-60s Fahrenheit. There’s Dolores Park to lay out in when the sun actually decides to shine; music festivals that carry on no matter the weather; and occasional days when Karl the Fog is on vacation and we actually remember why we love living in Northern California.

For the most part though (or at least IMHO), it’s pretty miserable to spend your whole summer in SF. Luckily, or unluckily (?), for me at the start of the summer I went through a breakup that was just the “get the hell out of dodge” kick in the pants I needed.

I decided to offload the majority of my belongings and spend the rest of the year exploring and working my way around the world, I’ve been looking for places to live and connect with other people who share my same passion for doing good work without all the tethers that used to keep me in SF.

It didn’t take long for me to start hearing about Roam, and since I stepped foot into their Miami house, I can see what the buzz is about…

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The Beauty of Living with Less

living with less

In May I moved out of the house I shared with my ex. It was a great spot, furnished beautifully, and spacious—a rare luxury for downtown San Francisco. The heartache of leaving a relationship of three years was compounded by the anchorless feeling of no longer having a place to call “home.” For the first few weeks I hauled several bags and containers from one friend’s apartment to another, silently cursing each time I had to repack all my worldly belongings and lug them to another location. Then something amazing happened…

I 80/20’d my life and learned the joy of living with less…

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Silicon Valley Has a Vulnerability Problem

vulnerability A few of us sat in a swanky restaurant, the air was warm and smelled faintly of the honeysuckle growing outside. Glasses clinked on the patio and a group of dilettante’s tittered over a handsome young waiter’s joke. The general mood of the place felt like a modern day Gatsby party… except to me. I was trying to keep my breath steady as a deep, angry blush crept up my neck as the man across from me continued…

“Well, I just don’t know how you could have made those mistakes, being CEO. I am a CEO now and I would never let that happen” he said.

Breath in, breath out. I nodded, shrugged my shoulders and after a long moment responded “I guess you’re a better man than me”. The table nervously laughed and I mentally checked out until the dinner was over.

I had been brought out to discuss joining this CEO’s company for some contract work. Over the past few days I had surveyed the company, talked to employees, and put together a detailed list of recommendations. There were a lot of “easy fix” problems but all in all the growth challenges were ones that could be handled as long as a strong culture and focus on community was in place.

But I had made the critical error. At dinner, someone asked what I would do to improve worker efficiency, I answered honestly. As I talked I could see the CEO’s face change, he was taking my feedback as a criticism of his leadership… I realized too late that I was dealing with an insecure, “alpha” male (the worst type). So before I had time to swallow a sip of red wine, he fired back a reply aimed to hit me where it hurt.

“…I just don’t know how you could have made those mistakes.”

In Silicon Valley, admitting mistakes and showing your vulnerable side is one of the biggest social faux pas that I’m tired of trying to follow.

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What is an Untethered Life?

untethered life

The word tether, as a noun, is defined as a rope, chain, or the like, by which an animal is fastened to a fixed object so as to limit its range of movement.

Human beings are animals, but the difference between us and the dog on a leash or cow tied to a fence is that we often choose our tethers. Those tethers cost us money, and many of us—sadly—believe that by collecting tethers our lives gain meaning.

What tethers us?

  • Debt: mortgage, credit cards, payday loans, college loans
  • Social obligations: networking events, “friends” we don’t really want to meet up with but feel we must, parties that we don’t enjoy but will feel FOMO if we miss them
  • Material possessions: more clothes/shoes than you need, anything that you either don’t actively use or don’t actively love
  • Work we hate: the 9 to 5 where you can’t leave your desk even though you would be more productive and happier if you were working remotely, the career you choose because of money—especially money that goes to buy you material possessions you don’t need or love
  • Unhealthy relationships: friends that tear us down, romantic partners that aren’t growing with us, any relationship that causes more harm than good… and yes, this can even be family members at times
  • “Shoulds”: I’m Y years old I should be married by now, I’m X years I should have a baby by now, I should go to college, I should… anything that you have to convince you should—versus innately knowing it is right, true or something you actually want.

Leading an untethered life is as simple as cutting out, or minimizing, as many tethers as possible. Instead of striving for material possessions (something that is proven to make us miserable), untethering means getting rid of everything you don’t either love or need (similar to the philosophy espoused in Maria Kondo’s book on tidying up).

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Life Isn’t Fair: So Why Play by the Rules?

life isn't fair“Life isn’t fair” I remember this refrain being seared in my consciousness early on in life. It’s a bitter-sweet memory because I can still taste the knot of staunch injustice that gathered in the back of my throat when my mother would dish it out; at the same time, I’m grateful that the inequality of life was shown to me at a young age because I learned a valuable lesson that many adults I know seem to still have not learned.

Life isn’t freaking fair.

Now that you know, deal with it. You can bitch and moan. You can try and make the best of the cards you are dealt… or you strive to become the dealer. Your situation may be righteously unfair – but dwelling on that fact won’t move your situation one iota in a fairer direction.

Instead, embrace the fact that life isn’t fair. When you do your eyes will open to a world of possibilities, one that much population misses while they focus on the injustice of their situation.

Life isn’t fair, so why play by the rules?

You don’t bring a knife to a gunfight and you don’t expect to win at a table where the dealer’s cheating. The “fairness” that people so often talk about is the idea that if you go to school and make decent grades you should be able to graduate, get a good job and earn fair wages. It’s the idea that if you worked 15 years for a company they should keep you around for the next 15 years. Don’t get me wrong, I love that notion, the idea of fairness but it is simple not a reality anymore.

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45 Epic Quotes for Extraordinary Entrepreneurs

epic quotes

Epic quotes, they are what I turn to when I’m running low on inspiration. It’s encouraging to look at those who have been there, done that and crossed the chasm successfully.

Usually I’ll spend some time reading the biography of a person I respect, or if I just need a booster shot of entrepreneurial gumption I’ll browse through some of my favorite quotes. Then I thought “why keep these little gems all to myself?”, thus: 45 epic quotes for extraordinary entrepreneurs.

Epic Customer Service Quotes

  • If we don’t take care of our customers, someone else will. – Unknown
  • If you make customers unhappy in the physical world, they might each tell 6 friends. If you make customers unhappy on the Internet, they can each tell 6,000 friends. – Jeff Bezos
  • You’ll never have a product or price advantage again. They can be easily duplicated, but a strong customer service culture can’t be copied. – Jerry Fritz
  • The way to gain a good reputation, is to endeavor to be what you desire to appear. – Socrates
  • Here is a simple but powerful rule – always give people more than what they expect to get. – Nelson Boswell
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On Asking for Help

asking for helpThe idea of “fake it until you make it” blows. It is the antithesis of vulnerability. It requires you to outright lie to those around you, or give the appearance of a life you’re simply not leading. Worst of all, it prevents you asking for help.

I have a problem with asking for help. It’s probably one of my worst traits. I see asking for help as a combination of annoying and weak. I hate to bother people, and I also hate to seem weak—or worse: needy.

So when things get tough, I try and suck it up. When people ask me how I am doing—even on my worst days, I will usually say “fine” or “considering pretty darn good!”. Sometimes that is true. Sometimes I cry alone in the shower instead of just asking for help.

Asking for help doesn’t mean having to ask for a lot.

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The Power of NO

the power of no

The power of saying “no” is truly a life-changing art. Especially if you, like me, have chosen the entrepreneurial path. There is a beauty and elegance in saying no early and often. It not only saves your time, but it shows respect for the time of those around you.

Who knew that just putting your foot down and hollering no! like a 2 year old could catapult you to new levels of success and adventure?

To be fair lots of successful people have lauded the power of no before. Psychology Today said “No is an instrument of integrity and a shield against exploitation,” and James Altucher credits saying no with saving his life. Saying yes is often glorified, but saying no is what separates the men from the boys so to speak.

“The difference between successful people and really successful people is that really successful people say no to almost everything.” — Warren Buffett

Now that the secret’s out, let’s break down exactly how you should say no, when you should say no and why that beautiful, little, two-letter word can totally transform your existence…

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What Does It Mean to Escape the 9 to 5?

escape the 9 to 5

Escaping the 9 to 5, it sounds nice right? But what does it really mean? I’ve spent the last seven years trying to figure it out. In my humble opinion to truly Escape the 9 to 5 one must:

—Work as an entrepreneur, freelancer or creative

—Master delegation and the 80/20 principle

—Enjoy freedom of location, even if you don’t act on it

—Embrace wonder and the simple joys

Okay, now let’s break it down. I write this as much for myself as for anyone else; because as I sit here in my local cafe by the beautiful South Park district of San Francisco I am restarting my own escape from the 9 to 5…

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