The Best Mistake I Ever Made

Editor's Note: In response to my good friend Kevin Fox, who shared on his blog today how the college selection process, aided by a youthful blunder on his part, helped launch his career. Unsurprisingly, I've got a similar story, and that makes it time to share.

In 1994, I was applying to colleges. The oldest in my family, I was the first to move on from high school, and beyond the occasional lecture from guidance counselors at school, I was pretty much finding my own way. My best friends and I essentially banded together, comparing SAT and ACT scores, and scoured the college ranking and comparison books, even mocking the terms "Selective" and "Highly Selective", used to separate the good schools from the great.

Money constraints and a non-perfect high school record wouldn't have led me too far out of state. My best friend and I eventually settled on UCLA as our dream school. He was going to major in Film Studies, and I had picked Communication Studies, as close as I could get to Journalism. I applied to UC Berkeley, UCLA and UC Davis, as well as Brigham Young University (BYU) in Utah, which would have pleased some of my friends at church, while keeping me intellectually bored, and, in the event of complete disaster, I even filled out a form for Chico State, playing the role of obvious safety school.

Between my friends and me, we thought we had the process nailed. I wrote the essay over and over and had it reviewed by my teachers, knowing I might be on the bubble. I packaged up the essay with all my materials and sent it in the mail on the first day possible to UCLA, Berkeley and Davis, along with $120, $40 for each of the three schools' admissions fee. For UCLA, I listed Communication Studies as my major, with Political Science as the alternate. Berkeley placed me with Mass Communications as my major and Political Science as the alternate. If I remember correctly, Davis was English.

Three weeks later, I got a thin envelope back from the UC Regents. Expecting some kind of confirmation, instead the letter included a $40 refund from UCLA - stating that Communication Studies was open only to junior transfers, making me as a freshman ineligible. As I had selected other UC campuses, and the Regents assumed each school of equal valor, they just sent me my $40 back, instead of what I thought was the more obvious move - moving my application forward with Political Science.

Needless to say, I was panicked, and nobody had any real good advice. I essentially reapplied to UCLA and sent back the same $40 admissions fee, with Political Science as my intended major this go around, but this time seeing the envelope leave my house near the end of the 30 day period, not the beginning. I'm pretty sure this didn't help, as open slots for the impacted schools became more scarce.

In the ensuing months of my senior year in high school, we all played the waiting game. BYU was the first to respond, and I got in. I didn't see that as a big deal, although many friends of mine from church had received rejection letters. Chico State let me in, to no surprise. But the big wins were to come in March, from the UCs, especially UCLA, as my best friend and I shared these aspirations of being roommates and challenging one another for four more years and as we started our careers.

Come early March, Davis led off with a big fat acceptance envelope. I remember marking off an X in the Yes column on an index card at home, with UCLA and Berkeley yet to respond. I was 3 for 3, with 2 to go. But the next day brought a big shock. Instead of the big envelope, a small one from UCLA came with the well known refrain, "We regret to inform you... blah blah blah... lots of applicants... don't let the door hit you on the way out... blah blah." I was stunned and felt hollow - faced with the concept of not being with my best friend, and facing a reality of having to pick between the nearby but non-thrilling UC Davis and the complete life change that would be shipping off to Provo to be a Cougar.

This being at the very beginning of the era of constant communication, I had my mom's cell phone, playing chauffeur for my younger siblings, so I couldn't call her, and when I called my best friend, I just started to tell him before the reception was so bad that hung up on me. I was devastated, and it's all I wanted the world to know - that my dream had been dashed. In the days afterward, as I saw other friends get their welcome notes into the Bruins fold, the school counselors would pause their congratulations, turn toward me with concerned faces, and ask, "Now, how are you doing..."

After the promised deadline for acceptance letters, I finally heard back from Cal. A big, fat, glorious acceptance envelope filled my mailbox in late March that changed everything. My mom, lacking irony, exclaimed, "That's like getting into Stanford!" when I proudly announced I had the opportunity to become a Golden Bear, ruling out the Aggies of Davis and putting BYU way back in second place. The acceptance letter from Cal put UCLA as less critical, and started me feeling like I had accomplished something. I wasn't going to be palled up with my best buddy, chasing our dreams, but instead got the opportunity to stake out my future on my own at an incredible school.

Attending Berkeley ended up being a godsend, placed remarkably close to Silicon Valley as the tech revolution expanded through the first dotcom boom, and placing me with startups before I even claimed my double major degree in Mass Communications and Political Science.

Had I attended UCLA, I could have transferred into Communications Studies my junior year. It's probable my best friend and I would have even more great stories to share beyond those we still dredge up from high school. But it's just as likely we'd have met fewer people because we were too comfortable and cliquey. It's especially likely that I'd have ended up well outside of tech, and the unique experience that is the Silicon Valley. Maybe I'd have ended up writing for the LA Times or joined MySpace or Mahalo - spending my unfair share of time on the Web in Southern California and not the Bay Area. But my mistake of entering a major unavailable to freshman entrants changed my life - pushing me in a direction I'm happy with and continue to be fulfilled by.

As Kevin writes in his own parallel story, the mistake in the short term may have been awkward and disappointing, but the long term benefits of this choice ended up probably being the best mistake I ever made. By the way, if you're not reading Kevin on his blog or on his Twitter stream, you should.

Real Valley Stories: Rejecting the Closed Envelope

Editor's Note: Part 8 in an irregular series of stories from my 13 years in Silicon Valley. Part 7 talked about the leveraging your assets to get your way. This time, a real example of knowing when you're undervalued, and how to get what you deserve.

Not every Silicon Valley company has a smooth trajectory, and neither does the average career. Startups fail and career paths stall. You can run into bosses that don't get you, miss promotions, or find yourself excelling as a rare star at a company that simply isn't going anywhere. Fairy tale stories are often just that - fairy tales. In the real world, you need to be executing on what you've been asked, but constantly assessing your place, if you are rightly fit, or on a path to what you want to achieve.

Being a long-time employee for most of the last decade at a startup that went through many funding rounds and saw a practical carousel door in the VPs and CEO office, it probably comes as no surprise that I accrued a solid amount of company history and irreplaceable knowledge, but had to continuously reprove myself to new people who had just joined. Sometimes, the convincing was easy, through consistent work, but other times, it seemed nearly impossible, as if we were two people speaking a completely different language.

If explaining one's work product or role in a shifting company was hard, it was equally challenging to assess if an employee was compensated appropriately relative to their peers, if promotions had regularly taken place, and if one's stock options were valuable or worthless, depending when they came into the company, what round of funding we were aiming for at the time, or how well they had negotiated coming in the door.

After one recapitalization round, which had essentially wiped out our existing shareholders and started over, I found myself in a meeting with our VP of Marketing, talking about my job performance and how the company planned to reissue options to employees so we weren't completely underwater, having watched our existing stock reverse split to hell. As he tried to put me at ease that I was being taken care of, he reached forward, past his computer monitor, to a stack of white envelopes, the top of which had my name on it.

Inside the envelope, presumably, was the latest stock option grant - a new gift of shares in the company, which, once again, would maybe be worth something if we went public or were purchased, but were just as likely to expire worthless, as all the others had. As he lifted my envelope up and tried to give it to me, I interrupted and said, in a rare point of clarity, that I didn't want it, and no matter what it said, it wasn't what I deserved.

This startled him a bit, and I explained that I was familiar with how stock options were allocated, with the CEO and board of directors taking their share after the VCs had their stake, followed by the senior management team, the VPs, the Directors, and eventually, the working stiffs like me. I knew that my previous humility and hard work had set me up to get screwed, again, because I hadn't fought harder for a bigger title and all the rewards that came with it, from salary to stock.

Following on, I addressed the issue directly, saying I'd never been one to fight for promotions and titles, that I just wanted to do a good job, but that I had seen the only way one could get promoted or get a raise at the company was to solicit an offer from a competitor, only to rescind it later. I looked my boss straight in the eye, and coldly said, "Let's skip that step."

The move was a gutsy one, but one I felt I had every right taking, having committed untold hours and several years of my career already into the company, without being promoted, and getting the stock options others with higher job titles were no doubt getting. My boss and I spoke further, and he heard me loud and clear. The envelope went back on his desk, and we wrapped the meeting, my heart beating quickly, but my mind feeling steady. As I headed back to my desk, he did exactly what I had hoped he would, taking a two door trip down to the VP of HR's office to discuss the situation.

A few weeks went by, but shortly afterward, I was invited back into his office, this time with a plan that included a new envelope, with new numbers on it. In addition to the new stock options offer, I was given a promotion, and a plan to work my way into a second promotion the following year, that would see a commensurate salary increase and stock option bump. As time went on, true to his word, and due to my own efforts, of course, that too took place - as the company, with my VP, recognized the value I had brought for years, and continued to bring, and helped me take on more responsibility and finally be compensated the way I thought I should.

As I wrote in July about leveraging one's assets to get one's way, the risk I took was one where I was arguing from a position of strength. I was confident that I was delivering good work that I could be proud of, which could be measured. I had seen other great colleagues get stuck in their careers, and have to get alternative offers from competitors before seeing a career bump with our firm. I knew nobody wanted that headache, and that I could get other jobs if my brazen act went sideways. But it didn't. I knew the sealed envelope didn't have what I wanted, and I knew I was in the position to call them on it.

There are times to be humble, to keep your head down and do your work. There are sometimes economic realities at companies and industries which might prevent you from getting what you think you deserve. But if there's a mismatch between what you're delivering, and you see an opportunity, assess where you are and take the opportunity to make it right. Good people and good companies never want to see the strong talent go out the door, and happy employees usually end up working even harder and being more loyal. I'm glad I finally found a VP who got it and was willing to listen. And that's a real Valley story.