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Entrepreneurs and Relationships An Emotional Minefield


I love my family and friends.

And, I know for a fact that I wouldn’t be anywhere near where I am in my entrepreneurship-focused path right now without their presence and strong support over the years – especially when things got challenging, uncertain, and downright scary.

As humans, we’re definitely not meant to face life and it’s challenges alone – we are designed to be social animals that thrive on interdependence. We tend to operate optimally within the context of a larger tribe.

Ok, now the feel-good, politically correct version is out of the way.

Your closest friends and family members can absolutely be the most dangerous minefield you will have to traverse on your quest towards living on your own terms – crafting a lifestyle built around what truly makes you come alive.

How’d that feel? Probably not great, right?

Okay. Fine, you might have a negative reaction to reading that, but sometimes ripping off the bandage of the “feel good” version of the story can save you gobs of heartache and wasted breath later on, so listen up.

How many of the following scenarios have you found yourself facing, in your desire to break out of the norm and pursue a completely different course for your life?


Picture this – Your parents are both highly successful and respected professionals in their field. They might be doctors, lawyers, accountants, engineers, or college professors – whatever. The point is, they made a decision to follow a clearly defined path to traditional success and it worked out for them.

So it worked out for them and they got all the trappings of a stable and socially acceptable career – Promotions, 401k plans, fancy titles, vacation time, etc. Hell, maybe they even deviated from the prescribed path and started their own business, built around the skills they had developed within their field.

I still remember the look on my dad’s face when I told him I had no intention to apply to Law School, and would instead be buying a one-way ticket to South America in an effort to shake things up.

The hardest part of that conversation with my dad wasn’t his direct criticism or negative commentary.

It was the deafening silence.

Where once there was plenty of support and encouragement, I was now on my own, with no parental safety net. Would I go back and change that decision if I could?

Not a chance in hell.

“It is in our moments of decision that our destinies are shaped.”
-Anthony Robbins

I believe that the path to truly OWNING your life’s destiny is defined by difficult, often unpopular decisions.

The more we try to convince those around us that a decision is right for us, the more resistance we tend to encounter, and we weaken our own internal signal – the only one we need to listen to.


I still remember a painful breakup that I had to initiate, due to deep dissatisfaction with the direction my life was headed.

Here was a gorgeous girl that was deeply in love with me, who wanted to spend more and more time with me. Yet, something was off and I knew it.

I was living a lie, pretending to be something I was not.

I was making great money, but losing my soul to a corporate job that was demanding more and more of my time, energy, and health – while my side projects were forced to take a backseat.

Hello Relationship Friction & Arguments

Things got dicey when I mentioned the idea of quitting my job to start a business that would allow me to travel the world. Apparently, the image of the successful and stable guy with a great job was part of the package she was looking for in a long-term partner.

The problem with that guy, who looked perfect on paper, was that his very existence created a massive value conflict within me – which manifested as increased anxiety, irritability, and depression. Not good.

If there’s one major takeaway for how to blend the two worlds of an adventurous life and successful intimate relationships, it’s this –

Make sure your damned values are in alignment.

If you crave adventure and freedom, while your partner deeply desires a sense of stability, security, and routine – Things are going to get rocky, sooner or later.


This one is tricky.

These are the guys and gals you have shared some of your best times with including college, parties, support after breakups, getting that first “real” job, road trips, hangovers, and mistakes as you bumble your way forward into some semblance of adulthood.

However, if they know you simply as their good buddy who can drink most people under the table while also being a solid wingman – they’re going to want to keep you in that box. That’s who you were when they met you and that’s the person they are comfortable with.

I remember the time I told a friend of over 10 years that I wasn’t satisfied with hating my life for over 40 hours a week with the only reward being zoning out watching sports and chasing women on the weekends. His response shocked me.

“Dude, everybody feels that way – Nobody likes their job, and that’s just the way things are.”

In short – Fuck that.

I felt a strong sense of defiance and desire to prove that statement as patently false. At the same time, I didn’t want to lose a friend over a disagreement over what was possible in life.

On some level, some of your closest friends will disagree with you making a change that would cause you to take your life to the next level. Its human nature to feel threatened when someone might outgrow us or potentially leave us behind.

As you make bold moves and step up more in your life – people are going to hate – that’s just what people do. It’s more challenging to deal with hate that comes from your peer group, especially as you are in the process of reinventing yourself.

In a strange attempt at a smart analogy, think of yourself as a piece of software. Your friends know you as John or Jane 1.0, and they’re comfortable with that.

Yet, inside of you, if you pay attention is a burning desire to grow into a newer, bolder version – version 2.0– the enhanced, re-launched version of yourself that makes their own rules for life and, more importantly, actually plays by them each and every day.

The funny thing is, the more you stick to your guns and go for what you want, the more respect and acceptance you are likely to get.

Difficult Conversations

I still remember one of the most difficult conversations I’ve had in my adult professional life. I had reached the point of no return. The pain of uncertainty had been surpassed by the pain of staying the same. It was my leverage point – and it’s how I kickstarted my new life.

I could not and would not lie to myself any longer – ignoring the values conflict that was eating me up inside.

I hated my job.

The 6-figure, “impressive title” job that I hustled so hard to land after investing two years of rigorous study in my M.B.A. program was killing me, and I couldn’t hide it anymore.

That day came much sooner than I had expected. After many conversations with family, friends, fellow travelers, and other entrepreneurs, I reached a tipping point with my current status as a Senior-level corporate employee.

My heart was racing and I was totally terrified, but I knew what had to be done. I called an impromptu meeting with my boss, and told him with a growing lump in my throat,

“I’m unhappy, and I don’t think this job and company are ultimately the right fit for me and where I want my life to go.”

Brace for impact.

To my surprise, he took it really well, and of course, had a lot of follow up questions. He even asked what it would take to make me reconsider leaving, what aspects of my job and responsibilities we could negotiate on in order to get me to a better place.

I didn’t see that offer coming, and I almost felt my resolve weaken.

In just about any other circumstance, I’d love to work with a guy like him. Whether in a start-up or some other smaller, more entrepreneurial organization, we’d kick ass together.

However, the time had come to only listen to me – for the first time in years.

I had become unemployable. I’m not cut out for the corporate grind, and no negotiation would take place. I was done. No amount of additional “corporate training,” transferring to another department, promotion, or extra vacation days was going to cut it.

It was time to leap. I followed through, even with shaky resolve, and handed him my letter of resignation.

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