The other day, I spent an hour or two crafting a job application for a senior project manager job. I had been following the firm for a few years: they are technical consultants to nonprofit organizations. Two years ago, I had come across some of their conference slides and blog posts, and the place just sounded like an amazing place to work. I reached out to two staffers and met them for info interviews. At the time, I knew that the core of their work was around Salesforce/Drupal. I had never held a position where I needed either of those skills, but I figured that moving towards Salesforce might be a good move for my future. I started doing training videos, etc. Even after I joined the university for the social media job, I attended the Salesforce conference on my own time and dime, and I occasionally took some online courses on Salesforce. After I crafted my application, I reached out to one of the info interviewee people, and then it hit me. As much as I think I want to work at this org and in this space, sometimes there simply is no way around the required time in the saddle. Taking video tutorials is NOT the same as using Salesforce at work. It was a sad but valuable realization, similar to one I had had months ago after I applied to the um-teenth corporate social responsibility and philanthropy job. I had been trying to learn things on my own on the side, but ultimately, when I got real feedback from the hiring manager, she said this: you have really robust skills and experience, but for this role, we have so many applicants with the exact skills who have been doing the exact role somewhere else. In other words, why would they take a risk and hire someone who would have to learn on the job when they could just plug/play a person with the exact background they are seeking?

So here’s my dilemma every time I pivot professionally: The job is X, and there are a ton of people with the precise skills of X. There’s no reason to have someone with Y skills learn X skills on the job. I feel like my skills match well for the intersection of tech and nonprofit and consulting. And I have worked in that space before. But managing tech features/projects for a scrappy nonprofit or a slow-moving government agency is different from working at a place that has the latest/newest platforms and that employs people who are certified in project management.

Today I feel tired and discouraged. Is this a repeat of my generalist vs. specialist problem? At some point, when do you throw in the towel? You think you belong in a certain space, but that space doesn’t think you belong. How long do you try to fill the gaps to gain approval and acceptance ? And when do you stop and say, maybe I can’t help in this specific capacity. Maybe I can help as a donor, but not as an employee. I’m not the person they are seeking. And maybe I have never quite been that person, bc I am an eternal misfit after all. Sigh.

I reached out yesterday to an acquaintance who’s a realtor (former tech company employee). I asked her about recommended places to take the required courses for the sales license. She got back to me suggesting an online outfit that actually has a rolling schedule. No school semester schedule with registration or add/drop periods! Granted, real estate has popped into my mind many times in the past, and given how many related tasks I’ve had to handle for my father throughout the years, this isn’t a total stretch. There are aspects that appeal to me: the independence, the different schedule, the various business elements, the balance of people/solo time, the potential for growth… Maybe now is the time to stop trying so hard to fit my square peg into a round hole. Maybe this path will lead to something satisfying and fulfilling. The timeline can be as fast as a couple months (the barrier to entry is low, as Bubbey says) and then I might know with clarity…