From analog to digital notebooks — Find the best note-taking tool for your needs. — If you were to see my office, you’d be greeted by a pile of notebooks on my desk. And that would only represent what’s visible — I have another stash of virtual notebooks on my computer. But my notebook collection isn’t random. Each notebook has a very singular purpose. And…

Don’t let your ideas get lost in the digital shuffle. — I’ll start with a disclaimer: I think ChatGPT and other generative AI products have a lot of limitations. In fact, as a writer, I think the output is pretty terrible — generic, repetitive, and all-around blah. But as a person who writes a lot, both for clients and personally, I’m…

Yes, you can run your business smoothly with a variety of projects. — You’ll hear this advice a lot as a freelancer: land a few big retainers and you’re set. You’ll only need to manage a few clients and your income will be more stable. While true, retainer arrangements have a lot of drawbacks unless you have an absolutely perfect client. Rather than…

You can choose the people you work with. — Phase One of building a business is finding clients. That’s a given: you need a sustainable livelihood, whether you’re running a business with employees or working as a solopreneur. But Phase Two looks a little different. You have enough work and can afford to be choosy about clients. That might…

A vital component of local economies. — My first job was as a bank teller at a small-town bank. The bank sat on the corner of one of the town’s main intersections, and when I say “main intersection” I mean one of two stoplights in the small community of 3,500 people. The bank opened in 1906 and…

A good boss can’t protect you. — “People don’t leave bad jobs, they leave bad bosses.” (Or so the saying goes.) Does that mean you should stay in a bad work situation if you have a good boss? I once worked for a terrible company. All the traits of a toxic work environment, with senior employees bullying…

I’m not going anywhere. — Yesterday I went on a solo trip to the Art Institute of Chicago. In my many, many years of living in a Chicago suburb and many, many trips to the Art Institute, this is the first time I’ve gone alone. I could have taken my family. The kids don’t have…

Stand out in a sea of online writing. — You can’t go anywhere on The Internet without reading about AI content these days. And while many tools promise to “generate content faster” savvy writers know that quality content will ultimately win the attention war. But what does “quality content” mean anyway? Great writing, sure — content that contains nuance…

Combine buyer psychology and realistic expectations. — It’s a natural instinct to “pitch” ourselves to new clients. Fancy deck. Lots of testimonials. A discovery call where you try to convince the prospective client that you’re the best person for the job. But is persuasion even the right approach? In the book The Win Without Pitching Manifesto, Blair…