This is a tough question, really. It got my mind working in overdrive.
I spent about 25 years developing a career, from general retail to high-end menswear, then learning the basics of management and merchandising. I took those skills and transferred them into what can loosely be called Home Fashions, beginning with furniture retail, then learning much more about how furniture is ordered, priced and displayed; simultaneously with that I learned key skills in how to manage a team of sales professionals. I loved my work and was justifiably proud of my success.
But furniture's a difficult industry, and sometimes "success" means bankruptcy, at least for the principals if not for the staff, who shift between the large corporate stores and the smaller, more specialized entrepreneurial ones. So I adapted, ultimately choosing the greater opportunities for creative exploration through the smaller, specialized spectrum of the market.
I managed a design-trade-only showroom for a small local manufacturer, and I helped launch a very trendy boutique/gallery where the furniture was treated like art (some of it actually was art). I represented small, seven-men woodworking shops from Vermont in fabulous, jewel-box type stores in Cambridge, MA and New Haven, CT and developed unique gifts for customizing and selling one-of-a-kind pieces for people associated with Harvard and Yale (respectively). I also purchased soft goods (upholstery, fabrics, drapery panels, pillows, etc) as well as developing several unique, exclusive and exquisite lines of cabinetry from woodworkers and small furniture manufacturers as far afield as Maine, W Virginia and, in one case, Italy.
I learned that working in that industry meant having constantly to either live up (or down) to a certain reputation while constantly introducing (and reintroducing) myself to an ever-changing spectrum of players, place holders and rainmakers in any one given region. At times, it felt as though I was eating nothing but crow and humble pie, but overall I loved my job and my life in general. I was totally bought into the idea that my job equaled my identity, but not my self-worth: I always said that one's worth as a human being lies in one's ability to give and receive love. And I did plenty of both.
When working in CT, I injured my neck merchandising the 30,000 sq ft store where I essentially ruled the roost, and my recovery took almost a year and a half. That was when I decided that I needed to start afresh in a warmer place and relocated to SoFla. I really should have done my homework better, but I figured that my skills, relationships and experience were all transferable. That ended up being a fatal flaw.
It took nine months here in Ft Lauderdale to find a job I'd been qualified for in the mid-80s (in 2003-4); part of it is the reality of a market where custom anything is rejected over the expediently-delivered, part was the fact that I had no desire to eat enough humble pie to troll a huge showroom in a shirt and tie in search of victims rather than clients.
But surely a huge part was the cultural crisis of being a rather patrician (and correspondingly precious) New Englander in what I felt to be a backwater of conventionalized-yet-marginal taste and decorum. For the first time in my life, I utterly flunked interviews with a simmering contempt on both my part and that of my perspective employer.
When that last job ended in 2005 (through the usual path of bankruptcy, natch), I knew I was doomed: my career was toast. I knew the market well enough by then to know that I was the ultimate square peg.
My futile attempt to bond with a sociopath rattled my faith in my ability to attract and maintain relationships with decent (if flawed) guys; the three subsequent attempts have only confirmed it. This is not the place to find husband material, especially as I've never been money-motivated.
However, I've never had a richer nor varied circle of friends; my capacity for love isn't diminished, just the spread of possible, available beaux. I wish it were otherwise, but sadly it really isn't.
And my job now, though hardly "prestigious" by any standard, affords me a certain lifestyle. And as it's a somewhat high-profile position in the community, it comes with undeniable social advantages; I'm a known entity in a small (and hypergay) community. When a community is as centered around bars as this one is, working in a bar denotes a certain cache, for better or worse. And it defines me for most of the people who live around here, again with all the mixed blessings such a position implies.
But it has little if anything to do with my self-worth. I consider myself an author (which I hold in high esteem) with many fabulous friends, who happens to pay his bills working in a rather skeevy dive.