As I’ve been thinking more lately about the next 5-10 years of my career, I’m trying very hard to be confident in my abilities yet realistic. Everyone talks about “Impostor Syndrome” these days, thanks to Sheryl Sandberg (who clearly suffers from a case of it herself), but that’s not what I’m facing. Or maybe, a teeny tiny bit of my struggles is self-doubt and feelings of being and impostor, but most of that feeling is fact, supported by hard evidence. While I have some learned skills and natural talents, I’m not prepared for any sort of next step in my career – whether that be a step up, step sideways, or even down.

I’ve read numerous job listings, applied to a few just to see if I could get any bites, even partook in a couple of interviews as an exercise. While I’m not devastated that none of them landed at an offer (I am focused on adding value in my current role at least for the next year), I’m also hyper aware that I’m not setting myself up for long-term success.

This is not the first time I’ve written about this, of course, but every day that goes forward is another day passing where I imagine a future for myself of under or unemployment. Yes, I can definitely take steps to improve my prospects, but I feel like I need to commit to a clear direction before I move forward.

My social anxiety and general anxiety is crippling, yet I hate using that as an excuse. But any job that requires constant nurturing of numerous social relationships is not for me. This pretty much excludes most, if not all, senior-level marketing and business development functions. There is a small space for someone like myself as an expert in content production and data analysis, the later area which I can certainly improve in, but I’m not sure I want to spend my life dedicated to hiding in a cubicle crunching numbers.

That leads me back to the question of whether I want to stay in technology to begin with. I completely fell into tech, and I’m glad I did, but it’s also an industry filled with highly intelligent, well-pedigreed individuals who are so talented at learning quickly and effectively to continue optimizing their daily process and deliverables. That said, I do really enjoy working in an industry that values brainpower over fluff. I could have ended up working in media given my background, maybe even having found myself in LA instead of San Francisco after college, and I imagine now I’d be lost in how to move up inside a highly social, “who-you-know” relationship-based industry.

Nonetheless, in Silicon Valley, those who succeed without seriously high IQs are brilliant on the people side, and as I’ve already stated, while I’m an extrovert my social anxiety limits me greatly on this front. I cannot have a job that requires me to go to drinks and sustain conversation with a business partner, prospect, or industry analyst. I might be able to do this once in a while, and at times enjoy engaging with other people, but the amount of stress it causes each time I imagine must cut into my overall life expectancy.

Even if I was to successfully obtain, say, a content marketing manager job in the future, where does this lead? At 20-something, content marketing is a good role because it exposes you to a lot of areas within marketing and business overall, and then you can pick which to pursue. That said, a good content marketer looking to move up the food chain will have similar options (and limitations) to what I have today. The content marketer could just build out a team of content writer in a large organization and manage global content strategy – which is a good and important job but seems to end at that. I don’t think I’d feel fulfilled in a role limited to content creation. Or, the content writer could move into a more external-facing role, but I’ve already discussed that I’m not suited for such a position.

Work is work, yes, and no job is perfect. It’s possible over the next 10 years, when/if I have a family I’ll realize that my “kids” are what’s most important and my job requirements will shift dramatically. Perhaps then becoming a terminal content marketing manager with clear deliverables and reliable hours will seem more than palatable. Or then I could freelance as a writer and charge heaping fees for each document I create, which by then would be high-quality due to years of high velocity output for some global 2000 technology organization. Maybe I need to tell the little girl voice who wants to change the world to shut up because it’s time she grow up and find a stable, albeit unsexy career. I’ve spent too long at startups that no one has heard of, and this makes me unemployable.

This is what goes into getting hired in a non-technical position in Silicon Valley, from most to least important:

1. Pedigree: Where did you go to school and what company’s have you worked at in the past? What was your degree(s) in? One successful company that is respected, even if you spend just one year there, helps greatly. (If there were some pedigree score on resumes from 1-10 I’d say at this point I have about a 2.5.)
2. Analytics Savvy: Can you speak data? What results have you generated from your work and how did you measure them? How can you use data to add more value to an organization?
3. Social Skills: Are you able to maintain a hour-long conversation with different types of people on topics ranging from how great they are to last week’s football game? Do you come off as not somewhere on the autism spectrum*? (*The tech industry has plenty of room for people who are brilliant aspies, but mostly in technical roles. However, if you are very strong in analytics than this is acceptable and expected even in a non-technical role.
4. Writing Ability: Can you write in complete sentences? Have you ever created any collateral which drove quantifiable results (sales revenue metrics are best if you can figure out how to measure this.)
5. What Have You Done? If you pass all of the qualifying items above, then, and only then, does what you’ve actually accomplished matter.

So if I want to stay in Silicon Valley I need to work on at least #1 and #2. I’ll never be strong at #3. I’m ok at #4 and can focus on improving this in my current role. For #2, I want to figure out how to become a quant-minded marketer. I’m trying to get the right analytics set up to measure goals and such, but I don’t know where to start. For #1, well, I think my goal needs to be really beefing up my analytical skills in order to obtain my next position at an established, soon-to-IPO startup. I desperately need that at-least one year of a success on my resume to be taken seriously in the Valley. Alternately, if this still proves impossible, I could get an MBA in order to get into one of those “just about to be successful” companies, but that requires getting into a Stanford or Harvard, which is just as hard if not harder (esp as a 30-something.)

So I just am taking a hard look at myself and my future to decide how badly I want this. It’s not like if I go into another industry suddenly I’ll have a clear career path and not have to work at it, but I have a feeling that outside of tech there’s a bit more opportunity for people who aren’t former valedictorians and student council presidents. I definitely can make something of myself here – I feel I’ve established a wavering baseline of competency as a tech marketer – but it’s going to be a lifelong uphill battle. Yes, it’s even harder as a woman, with few female role models at the top to look up to (not that I’m a typical woman and not that I get along with women anyway, but it is what it is. There are additional unspoken limitations when you are female and cannot have a close yet informal mentor relationship with a senior executive without dirty looks from fellow employees.)

I really need to figure out how much I want this. And what is “this” that I want?

Well, this is what I want, but can I get a job that fulfills this, and how on earth to I pivot from communications to something that does:

• To create a product or experience that many other people use and that improves their lives
• To be able to get to the end of my life, look back, and think of all the great things that I’ve built (or been a part of building)
• To disrupt industries that are inefficient and limit value to the everyday person
• Enough money to afford a house, infertility treatments for 2-3 kids plus the resulting 2-3 kids, international vacations at mid-tier resorts
• Time to spend with my future family, traveling, painting, writing
• Being around smart, witty people all day and laughing whenever possible
• *Or, maybe, I just want to take a road trip to anywhere, picking up stories and experiences, and become an author, somehow, and creating stories that address psychological and sociological issues generated by our current and future technologies and economies… hmm.