Putting "I" back in "team": What I learned from my transition from entrepreneurship to intrapreneurship

“I swear to God, if I see one more job description that says the organization wants both ‘an entrepreneurial, creative genius’ and ‘a collaborative team player,’ I’m going to snap!” I cried to a friend. “The worst part is that when they find that rare combination, they don’t even recognize it!” I was frustrated, and beyond exhausted, but the veil was beginning to lift, and I knew what was being revealed was important. Now, months later, I’m at last ready to share what was illuminated...

Since it is one of our primary values, it shouldn’t be too surprising that one of the ways that it is evident that we Americans are people of extremes is in how we work. The unspoken, contradictory “rules” we are taught by our culture starting in grade school are to fit in, to conform and to be exceptional, to win the competition. By the time we are adults we take these rules for granted, perhaps not even noticing the ridiculousness of it like we once might have at lunchtime and recess. But it persists: Don’t make your colleagues uncomfortable by speaking up, but be sure to get recognized. Don’t challenge the status quo, but be innovative. Be a “team player,” and be “entrepreneurial.”

It may be “normal,” but I think it has also become overwhelmingly obvious that these oppositional goals aren’t working for us. So many of us are aching to “abandon ship” (71% according to this report) because the organizations we work for demand we not only give or most precious resource, our time, but they also want to own our minds, hearts, and souls, they want us to be a "company woman." Those of us who indeed launch out on our own might hope for reprieve but instead quickly find ourselves faced with at the very least burnout and at the very worst deep loneliness. We know that we are all out of balance and so have become obsessed with the myth of work/life balance. (As if we weren’t hurting enough from the failure of our economic system, this myth suggests we each are also responsible for independently alleviating the consequences of these failures!)

Perhaps you’re thinking, “Yes, but what am I supposed to do about all this?” To give you the answer you deserve, I will share with you some of the ups and downs of my own journey of discovering this deeply rooted problem and developing some possible solutions. (I’ve got a lot of ground to cover here so this article is longer than usual; don't worry, I've included lots of fun GIFs to make it a bit easier to digest.)

In my twenties I was as hardworking as any worker can be. Somehow I was consistently surprised by the tension I would eventually feel with each of my employers because I was the one who always wanted to do more than was I asked to. I wanted to dig deeper, to reach wider, to move faster, to rise higher. They, however, often just wanted me to refrain from asking questions, keep pace with the group, settle for adequate, and stop trying to raise the bar. This perennial tension ultimately led me to have three distinct careers and a slew of odd jobs - summing up to roughly thirty jobs in the span of a decade. I feel fortunate to have learned so much so quickly, but I was sadly also unsure of a way forward.

I often refer to myself as an “accidental” entrepreneur. Like many of my generation experienced during the recession, I found myself with a college degree and no job prospects. Because of my creative strengths, I found a way to adapt and make-do. Since I wasn’t being offered any full-time positions, I started taking contracts instead. Before I knew it I had a roster of clients (awesome ones too). I was officially freelance, a “consultant.” During this time I often heard from others “oh, you’re living the dream!” which always reminded me both how unhappy most people seem to be who are working in organizations and also how little people understood what it actually means to work for yourself.

I tried to share with others when I could that self-employment contains as many peaks and valleys as any employment. I too had once thought it would mean limitless freedom and autonomy, but what it actually was a very long, very steep journey of learning that freedom is always accompanied by responsibility and autonomy is impossible without mutuality. It continues to shock me how even though almost one-third of Americans are now self-employed in this so-called gig economy, countless cultural messages are still able to perpetuate the myths of self-employment that are not only entirely false but also incredibly crippling. (I honestly wanted to throw something at the radio when I heard an ad trying to persuade its listeners to become a rideshare driver on the heels of the deaths of Spade and Bourdain.)

It was brutally hard at times, but I tried to be grateful for I did feel like I could finally be my curious, audacious, ambitious self and I was happily finding that by doing so I was able to help others more than I ever could before. I do think everyone should experience self-employment for at least a year or two because it is the most powerful way to learn indispensable skills in resilience, confidence, courage, discipline, and patience.

At the same time, my work continued to take me deeper inside organizations, helping me better understand how they function and dysfunction. I had the great fortune and pleasure of working with many who are also paving a new way of working across organizations, breaking from traditional silos and building networks that challenge organizational self-interest. I am indebted to these brave pioneers for they showed me that not only are we incapable of doing it alone, but that we will do it so much better if we are together.

At some point, the feeling of being an outsider started to press in on me, though. I wasn’t sure if others considered me to be a part of the movement I was helping build in the same way that they considered their colleagues to be. I also observed other entrepreneurs limited by their self-involvement and I was wary of becoming one of them. Additionally, like any good marketer, I had spent years investigating what exactly the problems were that I was helping develop solutions for, and time and time again I discovered they were all related to collaboration. So naturally I asked myself: “Doesn’t it make the most sense to be working on these solutions inside an organization, where they can have greater impact?”

So began my journey to return to a more traditional job. Others’ reactions continued to reveal much: Just like those who’d shared with me that they’ve “always dreamed of being their own boss” had signaled to me that they must hate their boss, those who unintentionally insulted me by assuming that I was looking for a job because I needed to do so for financial reasons signaled to me the fears that kept them from striking out on their own themselves. As my fellow consultants reminded me of all that I’d miss if I did make this transition, I gleaned that in their own way they too feared change.

Was I afraid? Of course! What I was most afraid of was that after all the years I’d spent working hard to become someone who could live confident their strengths would carry them through, I would be asked to not be that someone, as I’d had in the past. So I decided not to let that happen, never to abandon that person I now knew myself to be.

I’ve been taught self-reliance from a very young age - my grandfather started supporting his single mother when he was ten years old living through the Great Depression in deserted West Texas and my grandmother raised nine children on a self-sufficient family farm in rural Kentucky - so it wasn’t easy for me to also take a deep look at whether being a “lone wolf” is really all it’s cracked up to be. (I am so grateful that I have had many, many teachers along the way helping me practice a better way.) So I also decided to try to be open to seeing what else might be possible if I leaned on others a bit more.

What it ultimately meant for me to make and stick to these decisions was submitting over 150 job applications, one by one, for over a year. I interviewed with 20 organizations, many of which I’d dreamed working for, all of which resulted in zero offers. Zero. I can’t tell you how many times I wanted to give up. But I had also made another decision: I wasn’t going to.

When a friend said to me “Wow, that level of rejection is soul crushing,” I responded, “Actually, it is soul birthing.” Because what I learned from this arduous painful process was priceless: Fitting the mold should never be the objective. And the goal should also never be to prove you’re the best. My dream, our dream, was never really about doing it on my own it was about doing my best. And our best is always better when we’re together.

I believe wholeheartedly that we can both be fully ourselves and be supported by one another. Because we can, this should be our vision for mutual progress. We should not be clinging to the outdated conformity norms of an industrialist economy nor do I feel we should we be fearfully reverting to the pre-industrial separation of tradesmen. I think because we have experienced both of these models for work in American history, we are now fully aware of the strengths of both systems and of individuals, and we can use this knowledge as we move forward.

There is a new model, a new cultural norm, needing to be born, waiting for us to heed its call. If we accept that it makes the most sense to strive for a middle way, we open the door to making different, albeit counter-cultural, choices and taking alternate, albeit sometimes frightening, actions. It won’t be easy. We will have to be open-minded, patient, and disciplined. We will have to remember it is worth all the risks, because the greater ones are the ones that come from believing in the duality of groupthink and every-man-for-himself, the ones that result in top-down collaboration and reinforced grandiosity.

If you’re inspired to begin, here’s some suggestions for how you might. Do the opposite of what you’re inclined to: instead of focusing on “getting it right,” look at where you’re stuck, where your beliefs are the most resistant to change. For example, if you have been working in an organization for awhile you may have lost sight of the big picture or, worse, who you are outside that context. Conversely, if you’ve been working for yourself for a long time you may have forgotten what really happens on the inside, or you may be avoiding the challenges that being part of team might present for you. If you’re looking for help, look inside your organization and look outside of it; if you have a gap to fill, consider using that opportunity to invite in someone who might have a set of strengths you don't have, therefore ones you perhaps don't understand, even ones that make you, dare I say it, uncomfortable.

As we transition to a new way of working with one another, things are bound to get ugly because we are all still grasping for what we’ve been taught to: wealth, status, and more traditional forms of power, which means we’re often still looking for ways to be “better” than one another, to bring one another down. When at last we have fully embraced our national creed of equality, we will finally see that the best we could ever achieve is interdependence, meaningful reciprocity, mutual growth. We will play life like a team sport with only one team: us.

We have to create this new way together - and we can't abandon parts of ourselves because we need what everyone has to offer. Because it turns out, not only is there an “I” in team, but it’s all that teams are made of: individuals with strengths, people who can contribute to the whole becoming greater than its parts. To me, this is the ultimate task - and the ultimate gift - of humanity.

What do you think? Leave your comments below!

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