I Think I Can, I Think I Can, I Think I Can’t…

I’ve come so far in my career and yet I know that I’m running up against a wall. The reality is that leadership roles in my industry are largely about relationships — earned either through sheer social prowess, consistent results (often secured through social prowess), or a combination of the two — and, while I don’t want to impostor syndrome myself into a tizzy — I’m just TERRIBLE at many of the key things that go into succeeding in my role. I mean, I am good at a small smidgen of the requirements of my ever-evolving job title which are buried and bashed to smithereens by my social ineptitude that goes far beyond simple neuroticism.

If I were good at my job, I’d have hundreds of people to call up and ask for favors when I need them, because I’d have a solid network of people in my industry who I’ve done favors for in the past, who are not only colleagues, but professional friends, or maybe just friends, but people who I’ve created bonds with, who I’ve shared drinks with, stories with, who I’ve brought into my network, and who, despite being busy in their own right, are always open to help in an ongoing exchange of friendly favors throughout our careers. Continue reading


Alcohol, Career Growth, and Getting Home

In 2011, when I was arrested for my first and only-ever DUI, I was driving home from a professional networking event. That’s not an excuse, it’s just that most people assume people arrested for DUIs are out partying it up club hopping or taking shots, which isn’t the case. I had one too many glasses of wine, waited probably about a half hour too short of getting in my car to drive, and clocked over the legal limit. Luckily, I didn’t hurt anyone but my ego and bank account. I learned my lesson.

That’s why at 8:08pm I’m sitting in the food court of a deserted mall listening to “Love Potion Number 9″ play over the loud speaker when I really should be at home doing a thousand other things I have to do. My company had a team gathering tonight and part of that gathering involved drinking. I didn’t go overboard — I had one glass of wine early in the night and cut myself off. But at the end of the evening my new boss, a fine wine connoisseur, pulled out a bottle of vintage bubbly, and it of the few members remaining at the table it was clearly rude to resist. And, I’ll admit, I wanted to try a sip or two — who am I to refuse the few tastes of luxury that are poured my way? Continue reading


On the Get Rich Slowly Adolescence Precipice

The other day, I was talking to my 23-year-old, soon-to-graduate sister about retirement. She was asking to borrow $300 to put as a deposit on a program and I was noting that she could keep the $300 if she put it into a ROTH IRA when she was paid for her hours. She didn’t seem all that excited in learning about IRAs, but I’m determined to teach her just how important it is to start investing in her 20s to take the first steps towards a reasonable semi-stable life in the middle class.

On a separate note, I’m living in the world of the wealthy, where somehow company founders walk away with millions of dollars from failed companies, while early employees who exercise their stock early enjoy virtual wallpaper. I always say founders deserve what they can get, if they can get it, so less bitter and more back to a realistic view about my own potential for wealth. Sure, for a few minutes there owning a large chunk of stock in a company was exciting. Anything was possible. ItĀ couldĀ have gone the other way. I mean, I knew it wasn’t going to for a variety of reasons within the company, but I kept dreaming. I got lost in the dream. Even if I wasn’t going to get rich off the shares, why couldn’t my 200,000 shares, priced at $.10 a share, turn into $1.10 a share (which, by the way, they were once priced at on paper.) $200,000 would, at that point, double my networth. It wouldn’t make me rich, but it wouldn’t hurt either. It certainly would make it more possible to afford a life in Silicon Valley. Continue reading


The First Page of the Next Chapter

Today I started my new job. I’m already buried in work, but I like it that way. The company is extremely different from my last, especially in its culture. I know that I’ll miss the fun, quirky culture of my last company, but one can’t stay in a job forever just because of the culture. I have such a great opportunity and I want to knock this one out of the park. I feel like I’ve paid for a startup MBA (in the form of early-exercised stock options) over the last four years, and now it’s time for the big leagues.

That said, I really wish I had a place to go at my office for quiet. While I didn’t love the cubicle culture of my old company, the whole giant room with desks and no privacy doesn’t help me focus on writing, which is a primary portion of my job right now. My boss mentioned he doesn’t mind if I work from a coffee shop or something but given the team is so small I can’t help but worry – at least for the first few months – that it would give off the wrong impression if I weren’t at the office all the time.

I’m excited to get my first paycheck as well. I’m now making – base – nearly what I was making with my full bonus at my last company. It remains to be seen if I can hit my full bonus here, but I’m going to work my ass off to get it, and if I can accomplish that then my salary will be $25k total more than my last company, and more like $35k over what I was actually taking home given the bonuses weren’t fully paid out as the company started to slow on revenues. I really can’t half ass my new job anyway, either I’m going to be a rockstar or fail miserably. I’m going to do whatever it takes to rock it. I’m focused on this one quarter at a time, otherwise I’ll be massively overwhelmed. At least the bonus structure is quarterly so that aligns with how I can set and track to my own goals.

There’s just so much going on right now, starting the job really made the whole next chapter of my life feel real. My neurologist has diangosed me with potential temporal lobe seizures and prescribed an anti-seizure med that I started yesterday. I’ve been packing like a maniac all weekend, as I have to have all my stuff out of my apartment by next weekend, and I’m also just dealing with the whole transition of moving to a new town that I don’t know, away from one that I’ve really grown to adore. The change will be good, though, and if I have anything to say about it this company will do very well and my stock options will buy me a house back in the town I love, where I can raise a family and have some sort of stability. In the meantime, I just hope my boyfriend proposes to me soon, because I’m about to give up on his ability to make that happen!



My $20,000 Lesson: Stock Options are BS

It’s been a while since I covered the bullshittery of startup stock options on this blog, but today life had led me to needing to put out a distress signal to anyone who doesn’t quite understand how they work and why they are really a load of fancy horse manure, slightly more valuable than a handful of lottery tickets.

What’s worse is those lottery tickets come with a price. I’ve explained this on my blog before, but feel like it’s necessary to cover this topic one more time, just to make sure that the point is clear.

When you join a startup, part of your total pay package is in stock options. For the sake of simplicity, let’s say you are a new employee, relatively senior, and you are going to be given $100,000 in total compensation. That compensation will not be all cash. Say you get $70,000 in cash, $30,000 in options. The value of those options is really where the bullshit factor begins. Options are priced at what the investors think the company is worth. The earlier the company, the lower the “valuation” (i.e. price the investors think the company is worth), but also there’s a lot of guesswork involved as well. What is the company going to be worth when it sells? How can anyone know that before the product is tested and it’s clear that people actually want to buy that product for the long term? Continue reading