Which Way to Go? The Career Ladder is a Maze

Throughout the last 10 years of my career, give or take, I’ve basically just gone where the wind blows. Each job I’ve obtained was the only option I had at the time. I’m not being overly dramatic here. I would interview for dozens and dozens of positions and finally when someone gave me an offer I’d take it. I didn’t really have the luxury of deciding what to do or weigh two or more offers against each other. I either accepted the offer presented or I waited weeks – months – years – more to get another offer. Waiting just wasn’t worth it.

All of that has left me in a career which — while I’ve been able to earn and save money — hasn’t shaped up to be a good foundation for whoever it is I want to be. It also hasn’t provided the experience needed to put me in that much of a better position each time I’m back on the market. That’s finally starting to change, but I still have yet to land an offer.

Right now, I’m extremely confused about what I should do next. I’m interviewing for very, very different positions in companies ranging from 25 people to 1000. Some of the roles have the potential of a VP titles, other director, and others manager. Part of me says “go for the VP role now” while the rational part says “you are not ready to be a VP and this is the time in your life when you should invest in being a manager for a larger, stable company to learn how to do this stuff right and/or broaden your skillset without everything being on fire all. the. time.”

I don’t have any offers yet, but I know that part of getting an offer is really wanting the role and pushing for it. Right now I’m interviewing for three positions and I just can’t make up my mind which one I would want. The VP role not only is a very senior position, but it also is with a company that is doing something really interesting and that excites me. But being a VP in a small company and having to build out an entire team while also executing on the day-to-day is probably too much for me right now. All I really want is the chance to focus on something (partially due and partially what I’ve done before) and do it well while learning how to do it better. A VP position will not provide that opportunity. I just don’t want to waltz into another failure. I have ideas of what I could do in order to do a good job, but I can see myself getting overwhelmed again.

But on the other end of the spectrum I could be very bored at a slower moving, larger company. Right now I think slower moving would be a good thing for me, but I’m not sure how long of that I’d be able to thrive in. I tend to do well in fast-moving environments, just ones where I don’t have to manage, build teams and execute all at the same time.

Then there’s the question of whether I stay in my specific area of my field or move into a tangential one, if I can get such an opportunity. I’m torn about that as well, although I’m comfortable admitting that I want to be closer to the product vs the more buzz side of marketing. Getting new customers is a useful skill but it’s a never-ending and impossible-to-win game. Meanwhile, figuring out what a market wants and determining how to tell the story of a product is at least intellectually stimulating and offers new challenges vs the same ones each quarter only bigger.

I mean I value this area of marketing a lot but I do not want to spend the rest of my life praying night and day that a reporter will decide to write about my company or testing the color of a button on a website to see – not if a product would be able to be used better – but if a few more people would fill out a form to contact a sales team. Again, I highly value the people who do that but I do not want to spend the rest of my life doing it. I’d rather be working in product but that’s a challenge given I don’t know how to code, so the next best thing is product marketing. That’s an area I can see myself really excelling in. And I’m looking to take a lower-level role in an organization to focus on just that. Yes, it also includes a lot of the less exciting dirty work (making dozens of datasheets for different industries, et al) but at least you get to be part of defining the story of a product and why its new features are valuable. You don’t just rehash the messaging someone else came up with. That’s the mind-numbing part of PR.. you’re a professional megaphone, and I don’t want to be a professional megaphone the rest of my life.

That said, I don’t have any offers yet, and eventually I might have to revert to megaphonism if that’s the only role I can get.


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