Your Entrepreneurial Spawn

Recently I found myself going through a bit of a ‘thing’ – in a good way. Certain forces within the confines of the CitySquares fortress have forced me to think about some exciting opportunities on the road ahead, as well as some challenges that I’ve never had to face before. And just as I’ve had to think about these good and exciting things, I’ve also had to think about worst-case-scenarios, as the market and economy put a damper on things and forced us to have backup plans. These things, coupled with a few family emergencies and close-calls, have caused me to shift my focus a little bit. You know how if you look at something bright for a little too long it can stain your vision for a short while? Well, think of entrepreneurship as the source of bright light, and the rest of reality as the backdrop to the stain. Let me explain…

As this company grows and gets closer to cash flow positivity, and as we continue to rack up traffic numbers, questions come to mind, like, “what next?” and “what does this really mean?” On the flip side, when the economy nosedives, and our primary markets stop cooperating so well, I’ve also been forced to ask those same questions but in a very different context. What a conflict! Furthermore, there was a very close-call with a member of my immediate family. These personal/family moments have a way of acting like gravity and pulling you down to earth very fast and hard sometimes.

So, these things have forced me to pause for a bit and think about who I really am. Because in either scenario, entrepreneurial success or failure, I am left with one single common denominator – me, myself, and I.

When you a third of your life dedicated to entrepreneurship, you inevitably become party defined by it. Things change. Your perceptions change, as well how others perceive you, including friends and family. Suddenly you’re no longer defined by the things that always defined you, but now you’re defined by what you spend 24/7/365 on – your business, your entrepreneurial drive. You are truly and without a doubt, true and through, an entrepreneur.

This changes you, and I’m not so sure it changes you for the better. Why? Because you lose a part of yourself. It’s unavoidable. When you put so much of yourself into one thing, for so long, you inevitably have to sacrifice other parts of yourself. It’s simply impossible to be an entrepreneur without sacrificing other parts of your Self. And when the business you create starts to take on it’s own life, its own characteristics, its own heartbeat and blood flow, suddenly you realize that it’s not a part of you anymore, it’s an entire entity unto itself. This entity is a being, if you will, that is the very personification of your entrepreneurial passions – its the result of it. It’s your entrepreneurial spawn, and it embodies everything that defined you.

I experienced this event, if you will, over the past several months, or rather, this epiphany. I had to ask myself, what if this thing actually, really, seriously takes off!? What if it really, actually, seriously becomes something!? What if it actually meets or exceeds my most realistic expectations? Or contrarily, what if it flops? What if the economy strangles it? What if outside influences and forces suffocate us? In either event – what happens to me? What do I do? Who am I, then?

So, here I am now, writing this post post-entrepreneurial-identity-crisis, I think. And I also think I’ve figured it out so some extent. I’m working hard now at trying to gather some of the missing pieces back together because I am not defined by my business, by my profession, by my entrepreneurial passions. I am defined by other things, who I am, how I treat people, how my family and friends view me, how my community views me. That is who I am, for better or for worse. I’m getting back to more balance in my life, and so far, I’m loving it.

The moral of the story is probably obvious – but just for the sake of clarity: As an entrepreneur, do not lose yourself. Do not lose sight of who you are and of the big picture, and of what’s really important in life. Maintain a balance in life. Many many years from now, when you are on your death bed, breathing your last few breaths, you will not utter words about how you wish you made more money, or how you wish you accepted that VCs terms, or shouldn’t have sold your company to Big Corp. You will think about family, about friends, about places you’ve been in the world, about those most simplest of things. So enjoy what your doing right now, and if you’re not, make a change.

I’m still trying to figure all this out, I definitely don’t have the answers. I may never have the answers! This is probably one of the big questions in life, ya know? I just know that I found a new perspective, and it’s working in the most meaningful ways.

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Get a Life

If you’re an entrepreneur, here’s one piece of good solid advice from another entrepreneur: get a life! Really though, seriously, for realz – get a life. You are not the most important person to walk the earth. You are not a big deal. You are not the next ______. You are not defined by your title, your network, the value of your founders equity, the extent of your LinkedIn network, your facebook friends, your twitter followers, your contacts in the VC community, the fact that you know Arrington or Scoble – who gives a shit about any of that! Ya know who cares? You. And that’s it. None of it matters, man! Get a life!

What defines you is the life you lead outside of work, amongst your family, and your friends (true friends, I mean). Entrepreneurship does not define who you are. It does not define you as a member of society, as a member of your community, your family, your friends. When you die, no one will say “wow, she was a great entrepreneur.” Your gravestone will not say “fantastic entrepreneur.” If it does, that’s just sad and pathetic.

I am an entrepreneur, but first I am Ben. I’ve always tried to maintain that perspective, and I’m fortunate to have friends and family who help keep me grounded, who slap me upside the head when I need a slap. And that happens here and there, for sure. But I’m usually the first person to slap me upside the head – I usually know when I need a reality check, I’ve learned.

So who are you? No really, who are you? What defines you as a person?

During these incredibly challenging economic times, what matters is not how many hours you’re putting in at the office – it’s how smart you are at working. Sure, it’s important that we all work hard – yes, we must work harder and smarter. And just because you work a lot doesn’t mean you’re working hard! There’s a very big difference. But now, more than ever, it’s also important that we practice some balance, some harmony – start with your family, your friends, some hobbies, do some of the things we enjoy outside of work. Put even more emphasis on balance.

What are those things? Spending more time with your family? How about going to see live music? Maybe its reading, painting, writing? Or is it skiing, bicycling, hiking, basketball? As long as it’s healthy – do it, and do more of it. And start right now.

Perspective

Today’s New York Times had a brief but attention grabbing article on its cover page titled “In Web World of 24/7 Stress, Writers Blog Till They Drop.” Greg Sterling responded before the sun came up in Oakland, Om Malik also responded, and Michael Arrington is quoted in the article saying, “At some point, I’ll have a nervous breakdown and be admitted to the hospital, or something else will happen. This is not sustainable.” It’s truly shocking to me sometimes how so many people I know, or know of, who are also so bright and intelligent, choose to work themselves to … well, to death. Don’t get me wrong, I’m including myself in at least the later half of that statement. I work 90% of the time I’m awake, and I, like Michael Arrington, have a sleeping disorder. I’ve been to neurologists for it and I’ve undergone sleep studies and the doctors ultimately conclude that I need to relax and get into a more consistent sleep schedule. So I’m guilty of it too. But I like to think that I’m getting better at it and that I do have some perspective.

Work can quite literally become one’s life, making the delineation between “work” and “life” nearly undetectable. Many of my own friends and family would say that CitySquares is Ben, and some might dare to say that Ben is CitySquares. Frankly, I find both of those assessments bordering on offensive, but I do understand their perspective.

What drives me might be different from what drives, say, Om Malik. What drives Om might be quite different from what drives Mike Arrington. And as an entrepreneur on my second business, and knowing many other entrepreneurs in varying stages, I can comfortably say that I know what drives me, but I cannot profess to know what drives them.

Over the past few year I’ve learned a good amount about balance too though. Sometimes a death in the family brings you back to earth, or the birth of a child – whatever it may be, but usually a major life event has a way of doing that – giving one perspective. I’d like to think that I don’t need a life event to remind me. Om Malik needed a heart attack to bring him back to earth. I’ve had some of my own personal wake-up-calls that I frequently use to keep my feet on the ground. I am constantly reminding myself that nothing is more important than family and health. And ironically, it’s precisely those two things that I’m working so hard for!

I’ve forced myself into a pattern of a fairly regular sleep schedule, which has significantly lessened the symptoms of my sleeping disorder. I’ve also learned to set time aside for the most important people in my life as well as time for myself. I’ve been practicing turning off the Blackberry, closing the lid on my laptop, taking a deep breath and just – letting go. But if I don’t practice balance, and it does take practice, than I start to forget why I’m doing all this, why I’m working so hard, why I choose this life – rather than this life choosing me.

This blog, Your Suspect, is most often about these very themes – these struggles between my own identity and Self, and my identity as an entrepreneur. I hope that this blog will tell a story one day, a story that I am living and that I plan on sharing with my own child.

I’m reminded of a line from John Lennon’s “Beautiful Boy”, Life is what happens to you while you’re busy making other plans.

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