The Career Game: A Quest for Success, Growth, and Opportunity

I wish I could get inside my colleague’s heads and understand what they think about their career progress. I might even feel more comfortable knowing their salaries even though this would undoubtedly lead to jealously. I’ve realized lately I spend too much time being paranoid about my career and growth prospects, while at the same time feeling so entirely overwhelmed by what’s on my plate that I wonder if I’d be better off requesting a raise or to trade in half my income for a direct report.

I could leave. I’ve had numerous companies reach out to me regarding job opportunities. Up until recently, I hadn’t pursued any of them. There was one with somewhat of a competitor to my current company that would have been at a higher level, but I turned it down because I felt I wasn’t ready yet, and mostly because I don’t have it in me to jump to a competitor. If I was to leave, it would be for a company that doesn’t offer products directly competitive to my current business.

But I’m in a bit of a tricky spot. As an early employee of a startup, you are often given stock options with a four year vesting period. Those stock options could be worth anything, from $0 to $20 a share or more. Employees that come in later tend to get higher salaries and lower amounts of stock options. But that’s not always true – sometimes they’ll get higher everything because the company needs them and they’re good negotiators. Then, with stock options, there is the dilution that happens when a company gets funding. If you come in early, you supposedly get a good deal because you can get a sizable chunk of options (in terms of % of the company) up front for a low-ish strike price, but then your percentage of ownership is diluted when the company raises more money. So if you own 2% when you join, after a few rounds of funding you may own .03% of the company, for instance. Granted, if the company is actually growing in value and eventually goes public or gets acquired, your .03% of that version of the company may be worth than 2% of the small business you joined. Odds of success are better than a hand in blackjack, but not by much.

I don’t work for the money. I never did. I’m passionate about growing companies. I like being able to make a significant impact on the company’s growth, and to disrupt markets. But, as I’m almost 30, and my boyfriend currently is unemployed with no savings, I’m starting to think about my future and how the next ten years are going to play out. I can’t imagine I’ll be the type of woman who wants to stay home with her kids all day, but what if I am? How can I best set myself up for a flexible career in my mid 30s when I’ll potentially have children and I’ll want to attend their school events?

So there’s that. But there’s also this sinking feeling of hopelessness, like I’m not good enough for where the company is now. I was a great workhorse, I was passionate and dedicated and mildly delusional with optimism all the things you be when you’re in a new company with extremely aggressive objectives. I said yes to everything I was asked to do. I pushed myself but I didn’t burn out because I felt like a key part of the team.

But now my company has grown to a point where the culture has changed quite dramatically. Expectations are even higher and there’s not enough staff to realistically support the goals, or perhaps I’m just not efficient and formulaic enough to perform at the levels the company wants. Yet, despite my lack of confidence in my work, they keep me around and I keep doing the best I can. I just wish I had more resources – like an actual team – to manage and to help drive success. At least recently we hired one person who, while not a direct report, is allowed to help with some of my projects. That has only added more work and expectations, since now I have help to do more.

So I’ve been exploring my options. Not on purpose. But after turning down the competitor who offered me a potential VP role, I decided I need to stop being stupid(?) about my career and at least be open to discussing decent opportunities that come along. If I ever want a promotion at my current company, it’s going to unfortunately have to come with an offer somewhere else. I hate that game. I don’t want to waste anyone’s time and I certainly don’t want to have to threaten to leave to be appreciated.

It’s not like I’m making chump change either, so it’s really hard for me to allow myself to want more without feeling terribly guilty. Who am I to expect or deserve $120k – $150k per year or more? And if I do get that kind of pay bump, would that actually make me happy? If I were to lose my job for some reason, wouldn’t that be harder to match in my next position?

But I know salary doesn’t have a lot to do with what you deserve and more to do with what you can negotiate. I felt I did a good job negotiating up front for a company that had not raised outside investment yet, but I have reason to believe  a peer is making $20k at least more than I am. But I’m not sure what their stock package is, or if I should even compare their compensation to mine as my role is a little less valuable in the organization. And I know I shouldn’t get caught up in wondering about that because it’s just wasted time, but without any opportunity for promotion it feels like I need to walk if I want to move up in my career. I tend to do that ever 2-3 years and it’s worked well so far in my life.

That said, there’s a lot I like about my job. As I said, it’s not like I’m getting paid chump change, and for what it’s worth I have a strong sense of loyalty to the company and pride in its success due to being one of the earlier employees. I greatly admire the people I work with, especially many members of the management team, and we’re still small enough where I get to interact with them all regularly. I know 99% of the names of people who work at the company, and everyone seems to know me as well. There’s still opportunities to make a huge difference in the success of the company, even if it means not having a social life and avoiding any personal engagements other than precious sleep. It’s safe, it’s relatively stable, it’s still exciting as the industry we are in is still in its growth phase. I can’t imagine leaving, but I also can’t picture where I am a year from now other than in the exact same place with no professional growth other than another year with the same story I have now. Does that matter? Is it better to move on to grow another company, so I can say by 2 years out that I’ve helped grow two companies versus one? Or is staying put more valuable at this point? And there are still all those unvested options that, despite potentially being worthless and/or paying for a downpayment on a house, are mine if I stay just another two years.

Two years is a long time. In two years I’ll be 31 and likely married. I’ll be trying to have my first child at that point. So these two years are especially important as far as career growth. I could stay, work my ass off, let go of any ounce of selfishness I feel, give up on asking for more pay and accept any that’s offered, focus on saving what I can from what I do earn, and just do the best job now so I’ll be set up for success later. I’m still learning, as there is much to learn about how companies function at this stage of growth versus the early stage, and my gut says stay, work hard, and the rewards will come later. The logical section of my brain isn’t sure what to think. Or do.

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2 thoughts on “The Career Game: A Quest for Success, Growth, and Opportunity”

  1. You don't work for the money? That's such BS. Please. You're so focused on having a security blanket of X amount of money that you won't buy a new car even though you're embarrassed by your current one. You want kids but are constantly pointing out how much it will cost you to have one with PCOS. And you want to keep the stay at home option open and yet your're going to marry the deadbeat who won't get a job.

    You work for the money. You have too. It's your security blanket and excuse for not making any changes in your life. You can easily afford a new car and to move out of your apartment but you're so focused on saving for a potential future that may happen (you're boyfriend is an idiot. stop supporting his ass b/c he is pulling you down) that you refuse to flip the switch and start your life the way you want to.

    1. @erin fair enough. I do work for the money, but what I meant was that there are other jobs out there with my experience that I could potentially get that would pay more. I could go work for a big company and getting a higher salary. So I work for the money, but that isn't the only reason I've decided on my job.

      I don't support my boyfriend. He has his own home (which he lives at rent free) and he's amassed enough in savings to pay for his unemployment. He's looking for a job now and hopefully he'll figure that out soon. I don't think he's pulling me down at this point. As long as he can get a job before we get married then I think we'll be fine. It's a little unfortunate that he hasn't saved a lot before that point, but many people enter marriages with debt – he has none. So it's not really that bad, he just needs to get on the ball soon so we can live a middle class life together in our 30s.

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