Riding the Emotional Roller-coaster


Courtesy of Mitch Loidolt / www.mitchloidolt.com

I have never thought of myself as an entrepreneur, but there I was last Saturday, attending aone-day workshop led by Jerry Colonna, a successful venture capitalist turned life coach, on surviving the startup life while staying grounded in one’s self. Given the emotional roller-coaster I’ve been on, it’s exactly what I needed.


In a room full of 30 or so participants, including seasoned entrepreneurs like the founder of Seamless Web and would-be corporate escapees getting ready to take the plunge, we introduced ourselves in turn and described what we hoped to get out of the workshop.

When my turn came, I said, in a quivering voice that took me by surprise, that I wanted to get a grip on the emotional upheaval that I’ve been experiencing since recently deciding on my “thing” — and to hang onto the drive and optimism that propelled me to pursue this “thing” in the first place.

Regular readers of this blog know that I have been on a journey in search of a fulfilling career after I quit BigLaw last summer. After a period of decompression and dabbling into various activities for personal enrichment, I realized three months ago that I wanted to become a local business owner (as I wrote in my second quarterly review). I didn’t immediately have a clear idea of the kind of business I wanted to own.

I did know I wanted it to be a brick-and-mortar operation. I soon figured out the industry I want to be in. I then zeroed in on the “thing” itself; it just felt so right. A clear vision of the end result – multiple shop locations in New York and beyond, run in an efficient and personable manner, servicing a tight community of clients – appeared before me, so vividly that I could hear it, smell it, taste it.

I shared my vision with a few friends. They told me that they could see the passion and excitement in me. Indeed, for the past few months, I have busied myself in learning about the industry and immersing myself in working to develop this “thing.” I even dream about it in my sleep. My head is full of ideas, ready to burst out.

My husband and I reached out to a number of business owners and identified at least a dozen acquisition candidates. They soon dwindled into a handful, either because the business was overpriced or unsound. As the pool of candidates shrank, my stress level increased. My exhilaration and enthusiasm soon turned into anxiety and impatience.

Then one candidate – my favorite – emerged as a front runner. The operation seemed solid. The gap between the asking and offering price seemed bridgeable. All we had to do to seal the deal was confirmatory due diligence, and then… I stopped myself from dreaming further.

I knew from my BigLaw experience that plenty of transactions fall apart at the last minute. The deal was far from done. Yet, despite my conscious effort to remain level-headed, emotionally I had already pinned all my hope on it. For a few days, I was on cloud nine, planning the changes I would institute after taking over. But first, the due diligence needed to be finished.

Even though there were four or five fewer zeroes in the price than my BigLaw mega-transactions, I pored over whatever information I could get my hands on. I waited eagerly for various documents to trickle in. How different it is to conduct due diligence for your own deal!

Before, BigLaw due diligence was akin to looking for pieces of rat shit in a giant bowl of chocolate chip cookie dough – a seemingly endless and mind-blowingly boring task. But as much as I had disliked the exercise, I did enjoy a sense of accomplishment whenever I had discovered the “shit.” After all, my work was a service to my client even though I didn’t get to eat the cookie. But for my own deal, I hoped and prayed that no “shit” would be found. I wanted the cookie badly.

And of course, I found something irremediable.

After being so close to getting what I wanted, I fell back to square one, with rising anxiety and frustration. I took the setback hard.

I was deflated. I thought that all the effort I had put into this venture was all for naught. Unlike in BigLaw where I would still get credit for billable hours worked on broken deals, I got nothing. (Later I recognized that all the knowledge I learned about the industry along the way was still valuable.)

This setback happened in the beginning of May. Instead of writing my regularly scheduled Q3 report, I allowed myself to wallow. I watched five episodes of “Bethenny Ever After” in a row. Although I find Bethenny’s voice and jawbone to be jarring at times, I started to have a new found respect for her. She built a successful product and business from scratch, and I could now better imagine how challenging it must’ve been.

To get myself out of the funk, I looked for inspiration on the internet. I searched for quotesabout failure. I also wanted to understand why I reacted to the setback – and the overall venture – so manically.

I think part of the reason was my eagerness and impatience to get started on the “thing.” After much reality checking with my husband, I knew this is what I want to do for a long time, perhaps even the rest of my life. If I had won the lottery or had only seven years to live, I would still pursue this “thing.”

I also craved a professional identity. I still dreaded questions like “what do you do?” and “what have you been up to?” I suppose I could say that I am an entrepreneur or businesswoman, but somehow I feared that until I actually owned a business my answer would only bring up more questions. I didn’t know how to answer these questions without appearing defensive. Perhaps I still cared about what other people thought of me and a large part of me still wanted to impress others.

More than a professional identity, I think the “thing” has become inextricably linked to my image of myself. Because it is my passion – the destination of a search that engendered this blog – it is representative of me. If the “thing” doesn’t succeed, what does it say about me? What am I going to do? It is like the line from Eminem’s “Lose Yourself” from 8 Mile: “success is my only motherfuckin’ option, failure’s not.”

In a way, I feared – and fear – failure deeply. Normally I have a healthy dose of confidence in my ability, especially in climbing the StairMaster in a structured environment. I have largely achieved everything I wanted out of high school, college, law school and BigLaw. Yet, it is precisely because I have never truly failed, I fear failure. I don’t know how I would react if and when I fail. And small businesses fail all the time. According to the US Small Business Administration, only one-third of new businesses are around 10 years after opening.

While I knew deep down that my fear was overblown – it is not going to be the end of the world if I don’t succeed in the “thing” the first time I try – the fear was nonetheless debilitating. I constantly second-guessed myself. It was easy to do so because I don’t have expertise in operating a business. I need to switch hats from a specialist lawyer to a generalist who is willing to delegate and be dependent on contractors and consultants. I must not only identify risks but also take them.

For inspiration, I read quotes like “success is going from failure to failure without losing your enthusiasm” (Winston Churchill) and “never confuse a single defeat with a final defeat” (Scott F. Fitzgerald). These quotes helped some. And I talked to my husband about my fear (which probably prompted him to tell me about the workshop and nudge me to take it), but I still felt alone in unfamiliar territory.

In the workshop, as people went around talking about their aspirations and fears, I realized that my journey is not alone. One person talked about the “absolute terror” that jolts him wide awake in the middle of the night. Another person shared his struggles to work at a sustainable pace without burning out. Almost everyone allowed themselves to be vulnerable, talking openly about how difficult it is to separate professional from personal identity and ego.

Jerry and his sidekick, Ann Mehl, spent much of the workshop talking about how to keep a more balanced entrepreneurial life by connecting with our inner selves and having courageous conversations within (sort of like my Hard Truths concept). I know it sounds new-agey, but it was what I needed to hear to renew my drive.

As I walked out the workshop, I told myself the following:

1) Let go of the artificial deadline of when I need to own the “thing”. If we don’t buy any of the remaining acquisition candidates, then I will start the business from scratch, an option which actually has certain advantages.

2) I will make mistakes and I will fail at times. They will just be detours in my journey and new experiences in themselves.

3) My identity does not reside in the “thing.” I am more than the “thing,” but hopefully it will, among other attributes of life, help me attain fulfillment.

4) Yes, I am an entrepreneur – a creator of value and an executor of ideas.

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