by T.J. Duwaik

     (March 1, 2001. San Francisco) I wrote a $1,000 check for rent today, which leaves me with $600. That's it. Six hundred dollars from a $100,000 bonus that I received after selling my first company two years ago. At the time, I assumed that I would be a millionaire by now--six years quicker than my father who first reached that milestone at 36. But, instead of busting down the door to the millionaire's club, I found myself sprawled on the wet sidewalk.

     I looked at my watch. It was 11:27 p.m. when I came out of the BART subway station and into the drizzling rain. Instead of going home, I turned in the opposite direction. I wanted to walk to the end of the world and jump off. OK, I knew there was no end of the world to jump from, but I didn't mind spending the rest of my life walking the earth in search of it. Besides, I could use the time to figure out how to deal with the pain that had resulted from two years of uninterrupted failure.

     I should have listened to my father--he wanted me to attend law school. He emigrated to the United States when he was 19 and started his own company a few years after college. As expected, the old boys network excluded him-- partially because he was a foreigner, but mainly because he was poor. But even after he became a millionaire, he didn't receive an invitation to join, which made him want to get in even more. He couldn't change his ethnicity, and money was no longer an issue, so he assumed the problem lay with his education. He should have been a lawyer.

     Of course, it was too late for my father, so he "encouraged" me to attend law school. In his mind, adding "esq." after a name conferred more than a degree; it anointed a person with instant status. Moreover, my father secretly hoped that I might one day run for President of the United States, a position that might finally garner an invitation to poker night with the Kennedy's.

     I didn't discourage my father's fantasies. I enjoy public speaking and I always gravitated toward leadership positions in high school and college clubs. So for the last ten years, I avoided tattoos, piercings, drugs, excessive drinking, and extracurricular activities. (This was before George W. became President, mind you.) And when I finished college, I felt that financial independence--to avoid the corrupting influence of special interests--offered an ideal foundation for a career in politics. So I followed my father's footsteps and became an entrepreneur.

     My first company, Planet Internet, was an Internet Service Provider in Denver, Colorado, which grew to a decent size before I sold it in 1999 in a stock transaction initially valued at $1.5 million. I was disappointed, however, since I didn't create the next WorldCom or Qwest, thereby obtaining all-important status (and making my dad proud). Nonetheless, I took my bonus and started two more companies, InterOmni and Optink, which were involved in privacy and consumer data. Both companies failed, unable to raise any capital.

     My fourth company, Greenhouse for Startups, exploded with potential, beginning with our first event held in October, 1999. A networking group for entrepreneurs, Greenhouse grew to 7,000 members with chapters in five cities. We obtained a ton of press coverage and considerable interest from investors; however, we couldn't find a revenue model. (Membership fees? Failed. Sponsorships? Failed. Fees from matchmaking startups with investors? Failed.) Like many other dot-coms, we couldn't find a way to turn the value we offered-- schmoozing--into revenues, let alone profits. And so, by December 2000, Greenhouse was simply another dot-com dot-bomb. Another failure.

*          *          *

     When most people look at dot-com entrepreneurs, they assume that we were greedy little fu--, um, buggers. Of course, money was a motivator, but many of us did want to change the world. To be honest, though, on a daily basis I wanted success because everyone around me seemed to be so successful. And with all the contacts I had developed through Greenhouse, failure implied that I had snapped defeat from the jaws of success.

     More importantly, my father's value (status) had seeped into my own value system. Yes, yes, I know I'm supposed to live my own life--but that's so much easier to say than do. I mean, I love my dad, so it's not surprising that I absorbed his values as my own--softened perhaps, but not purged.

     After failing as an entrepreneur, I entered the (real) 21st century with a revolutionary idea: work for someone else. This was not an easy decision for me since my role model (dear ole dad) hadn't worked for anyone for over thirty years, nor had I for the last seven. But I needed stability, predictability, and a respite--a vacation, if you will--from failure. So, I created a resume--my first since 1993--and began pounding the pavement.

     Alas, job hunting proved to be more difficult than fundraising. Investors look at both your bio and your idea, while employers, especially HR departments, look only at you. Actually, they only look at your titles. But the only title I've had through four companies and seven years was President & CEO. What else was I qualified to be? Business development director? Project manager? Perhaps a liquid transportation engineer (aka gas station attendant)?

     I rewrote my resume seven times in two weeks and sprinkled on titles like "Director of Marketing." Was it true? Well, I didn't have a director of marketing in my company, so I invariably performed that function. Of course, by that logic, I was also the Chief Financial Officer, VP of Sales & Engineering, and the MCSE Administrator. All these titles should have impressed somebody. (Besides me.)

     After 21 months of rejection as an entrepreneur, though, I was ill-equipped to deal with more failure as a job seeker. I worked my connections, obtained introductions, trudged through job listing Web sites such as Craigslist, Monster, and Hotjobs. Yet, I couldn't finagle a job offer.

     I hit my last wall in an interview with a venture capital group struggling to become an A-list fund. I knew a couple of the partners, so I thought that I wouldn't have to play the titles game. Moreover, they needed to build buzz, which is what I had accomplished with Greenhouse and considered one of my strongest assets. I became excited that if I helped raise the fund, then I might be hired as an associate. I would kill two birds with one stone: end the painfully depressing job hunt and land in a high status job.

     My first interview was held with a partner whom I had never met. Ruthlessly efficient and perpetually suspicious, she didn't interview me to learn my strengths. Instead, she investigated to uncover whatever I might be hiding. She probed, she prodded, and (I swear) she grinned whenever she forced me to reveal a chink in my armor. My titular faux pas? Not having an MBA.

     I didn't receive an offer, so I lowered my sights and tried to focus on my strengths: media contacts. Although few PR agencies were hiring, I felt that a journalist's referral would be golden. I added the title "Director of PR" to my resume, which--by my count--earned me a few points. But after a few interviews, I realized that I was losing more points for not having "PR Manager" and "PR Intern" in my prior jobs. What was I supposed to do? List my last three jobs as...

     I thought about tossing the (apparently) superfluous President title aside. But what would I say when asked for my direct report? "Well, sir, sometimes I reported to my twin, President Jad, but that got confusing. So, as a PR Intern, I usually reported to PR Manager Jad, who didn't get along with PR Director Herr Jad. He had a bad attitude and so President Jad fired Herr Jad's ass. We all got promoted and that's when I became the PR Manager. Oh, and CEO."

     I hit rock bottom and realized that I would have to start over at an entry-level position, with no status (forgive me, father). So I decided to enter the field that I had always wanted: writing.

     Unfortunately, the Internet destroyed the carefully balanced environment for writers by creating a plethora of paid writing positions, aka content creation. Pre-Internet, would-be writers overpopulated our planet, but the prevailing lack of fame and fortune kept the population in check, at their day jobs. Post-Internet bubble, the number of writers mushroomed and--perhaps a sign of Armageddon--this bastard population now had raised expectations. I'm sorry. I shouldn't call my new brethren bastards...but, dammit, those bastards had (paid) writing experience and I had none!

     Still woozy from the punches I took as an entrepreneur and a job seeker, a puff of wind could blow me over. So, of course, I got hit by a tornado. Well, perhaps "flurry" is more accurate, but it felt like a tornado--of rejections, ignored pleas, and friendly but discouraging responses. One journalist-friend, for example, said, "Listen, darling, writing is a tough field to enter. Have you considered programming?"

     I now had more notches on my computer monitor than my bedpost. Furthermore, my savings account was showing signs of waning interest and, before long, it would begin rejecting my advances. A quick check of my finances showed that I could pay my end-of-the-month bills, but my car payment, due on the 16th, would be a problem without the insertion of new funds.

     But I had nowhere to turn. My father, a consummate entrepreneur, had risked his fortune on a bigger fortune (more status) and now struggled with his own financial problems. I wanted to ask friends, but my true friends are just as poor as I, while rich friends aren't close enough. (Stupid integrity, I hope that you are satisfied.)

     My last hope was a personal loan. Unfortunately, many years ago, student loan problems blemished my credit history and, more significantly, I don't have any income. So, of course, my bank rejected me. Technically, they rejected my loan, but this time--as opposed to investors and employers--it was personal. I snapped and pretended that I hadn't heard from the bank. I even wrote my rent check today as if I were paying with Monopoly money.

     As I walked through the rain, the reality hit me. Hard. I couldn't get a job. I couldn't pay my bills. I had nowhere to turn for help. I failed. I failed when I followed my father's dreams (status). I failed when I followed my own dreams (writing). And I failed when I followed nobody's dream (a job). Each failure became increasingly personal to the point that...I failed as a human being.

     Have you ever seen the Whack-A-Mole game? Every time the mole sticks his head up, someone--all too happy to oblige--smashes the poor wretch back into the machine. That was me. The mole. Trembling in fear.

     As I plodded through the puddles, I searched the depths of my soul for something, anything, to build a foundation and take another risk. But I found only darkness. If I didn't have legs and wanted to stand up, for example, I'm sure I could have found a way. Desire can overcome anything, right? But, what do you do when you have the legs and no desire? Where, then, do you find the desire to overcome the absence of desire?

     I briefly considered suicide, but I'm too close to my family, especially my siblings. Running away--to Argentina since I'm a tango fanatic--seemed more attractive, but what would I do in a foreign country? Where would I live? How would I eat? Although I had no answers, Argentina seemed less extreme than suicide. And no matter how bad things got, I could always say, "At least I'm not dead."

     I had been walking for nearly four hours. My feet were exhausted and my brain felt as foggy as the San Francisco night. But one thing suddenly became clear: I had built my happiness, and identity, on what I was reaching for with my hands (success) rather than what grounded my feet (accomplishments). Consequently, my center of gravity was focused in my head, which made it impossible to keep my balance every time I got whacked upside the head.

     As I turned to head home, I started planning for my trip to Argentina . My two most valued earthly possessions are my books (nearly 1,500 titles) and music (over 400 CD's). But how many books could I take? Five? Six? Twenty? Certainly not enough. I could take a ton of CD's, but I don't own a portable CD player. And I couldn't afford one now.

     If I couldn't afford a CD player, how could I afford a plane ticket to Argentina ? Oh yeah, my dad's American Express. He'd be pissed off at me for leaving home with it, but what could he do? Deny me the blue card upgrade? Cancel my frequent-flyer miles? But--to what end? I wanted to take my books and music so that I could write. Couldn't I write here? What was I running from? And what was I running to?

     As I turned the corner toward my house, I looked at my watch. It was 6:45 a.m. and the sun was rising. I decided not to run away, but instead to quit the Internet rat race and simplify my life. I'm redefining success from titles, money, and status to friends, family, and happiness. I'm going to pursue tango dancing and yoga. I'm going to turn off the TV and light more candles. I'm going to take more seven hour walks--well, perhaps two-hour walks will suffice--and, in short, enjoy and appreciate life. And my accomplishments.

     Most importantly, I'm going to pursue my dream of writing, first with my newsletter, LiesDamnedLies.com, and later with a book. I don't need to be hired as a writer to be a writer. Of course, this means that money will be tight, but that's just an obstacle now that I've rediscovered my desire. Besides, I'll just pay my bills when I can pay them. There's not much my creditors can do since my credit record already sucks.

     As for my dad, I can only hope that he is as proud, as I am excited, about my story, Diary of a Failure, since it marks the beginning of my new career. And my new life.