What I’d Want in a Job

Outside of my first job out of college, which lasted 9 months before I quit, I’ve never worked as a full-time employee with benefits. I’ve spent most of my career working for myself, either running my own businesses or working independently as a real estate broker. It’s provided a lot of flexibility and opportunity, but it definitely hasn’t been easy.

Growing up year-round on Nantucket (as opposed to being a summer resident), it seemed completely normal for people to run their own businesses. There were no corporate jobs on the island. People ran their own trade businesses, operated restaurants, worked in real estate, and developed properties. My dad was, and still is, a successful building contractor/developer. Even when he was at his busiest, he had few employees and primarily worked with other businesses as subcontractors.

Perhaps the independence influenced me more than I realized, but I’ve hardly ever thought about working for another business again until recently. I know I want something new and I know how difficult it is to get things started on your own. It dawned on me that most people just look for a new job when they want something new. While it still takes work to find a job and start a new one, it’s nice to at least have existing resources and other people once you get started.

I’m keeping my options options open by both looking at job opportunities and getting a new business started. I’m being purposefully picky about the jobs that interest me. I’d rather take my time and find the right fit than run into something that doesn’t last long. Thus the desire to get things started, however slowly, on a new business simultaneously. Ideally, I’d like to find something that fits most, if not all, of the criteria below:

  • Good fit. Most importantly, I want a role where o feel like I’d be a good fit. I have an atypical background with pretty varied experiences.
  • Remote. More than just a remote position, I’d like a company that operates mostly, or even entirely, remotely. To me, the idea of only hiring people in one geographic location is outdated. Technology has given us all kinds of new tools to communicate and work remotely. Combined with occasional face-to-face meetings, I believe this is a key to keeping employees happy and productive.
  • Health benefits. A company that provides health insurance, particularly for employees entire family, makes be believe they actually care about their employees. This seems like one of the best benefits of having a job.
  • Forward thinking. Much of my experience has come in ecommerce and I’d certainly be interested in continuing as I believe it’s still a young industry. Additionally, I’m very interested in alternative currencies (bitcoin, blockchain, etc.), artificial intelligence (including chatbots & conversational commerce) and how we communicate (any self-published content platform). Of course, there’s a lot of tie-ins with ecommerce among these anyway.
  • Young and relatively small. I’m not terribly interested in working at a well-established company with thousands of employees. Much of what I worked would likely too feel too unnoticed. I’d prefer to work with a smaller team that’s somewhat still figuring things out and open to new ideas.
  • Innovative. Similar to above, I’d prefer to work with a company trying something new, either in the nature of the business, or how the business is run. There’s a lot of exciting new technology coming and I’d like to get a chance to use new developments.
  • Profitable or well-funded. For the reasons of stability, it’s nice to know there’s enough cash, or cashflow, to keep the business running for the foreseeable future.
  • Competitive compensation. Initial salary is less important to me than knowing that overall, a company pays competitively. That gives confidence that they want to keep people around and you’ll be compensated for doing a good job.

I’ve probably overlooked something, but those are the factors that are on the top of my mind. Some are less important than others and I realize it may be tough to find something that fits all of the above. It’d be nice to find the right opportunity, but I’m also ready to keep moving on my own projects otherwise.

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