Podcasts that supported my independence

I want to shine a light on some podcasts that I really appreciated as I made my bid for independence and went out to contract, consult and strap boots. Because in some aspects running your own business can be lonely. It suits me well but I also immensely appreciate having some voices that share my concerns, contribute to my thinking and sometimes just keep me company.

Underjord is my business and most of the work is me doing things. My wife does the books as that’s conveniently her profession and at times I’ve brought in people I’ve worked with when the budget allows. Now this isn’t the first time I’ve been self-employed but it is the first time I’ve continued to run my business, worked multiple clients, established separate revenue streams and generally buckled in for the long term. The other times I ended up an employee in a year or two after settling in with one large client. That was fine then. Now I’ve been going for two and a half years, I’ve had a number of different clients, some very brief contracts and consultations, some longer term engagements. I’ve weathered most of a pandemic, the birth of our child and moving to a house. So it feels solid. I planned to go independent and I have stayed that course.

Since my wife does work with businesses in her accounting work she gets the world of business very well. And since she and I share our lives and this business is an integral part of our personal finances she’s definitely invested. But even with her special incentives this sometimes frustrating thing holds true. No one cares about your business as much as you do. It’s not weird exactly but it can become painfully obvious when you try to talk about it with people who aren’t interested in business. Most people don’t even care about running a small business in the abstract. Even less about whatever your deal is. That’s fine. But it takes up a significant chunk of my mind and business owners I’ve spoken to share the sentiment. Being able to really get into it with someone who gets it is fantastic.

A good second best is listening to people that talk about it. And thats what I want to push for here in the form of podcasts. If you follow my newsletter I’ve covered a bundle of these there already. If you are curious about the newsletter you can sign up at the bottom of the site.

Focused (formerly Free Agents)

So this podcast has transformed from being about working as a free agent into a productivity podcast. It is a pretty decent productivity podcast but I’ll admit to missing the Free Agents and preferring the olden times.

If you want to run your own business and want to listen to people that do, go back to the older episodes and pick some that sound good to you. They hit on some good topics and I think it was quite helpful to verify and adjust my thinking on a number of things early on.

Hurry Slowly

This podcast is magnificent in a very understated way. It is strangely serene and lovingly crafted podcast. It sits in the productivity space. But for me this was very useful when starting my business as I have a brain that wants to go fast. And this podcast is all about pacing yourself. Spending the time to slow down, give my brain some time to work things through, consider some things carefully. The things I’ve done most deliberately are the things that have paid off the best down the road. I credit this podcast with a lot of that.

I would suggest starting from the beginning and then picking topics you like as you go a bit. It’s fine to skip an episode you don’t care about. Further along as show host Jocelyn K. Glei opens up more it can get a bit uncomfortable if you are a very skeptical person as she opens up about alternative interests. I think it has remained mostly good and while I’m quite skeptical of most of this stuff myself I value her perspective and I think listening to the less out there stuff in the beginning is valuable to anyone but I don’t expect my audience would appreciate the recent stuff without getting to know the more concrete episodes from early on.

There is especially one on transformative gatherings that I found incredibly useful. Because I know people that do these things well and I want to understand how to do it myself.


Very private YouTube creator CGP Grey and fairly public podcast network founder Myke Hurley talk productivity, apps and all that stuff. They get into business and independent creation quite a bit and I’ve found their thoughts quite useful. It also helps that the two are quite different and I don’t feel like I align fully with either of them which gives me a good spectrum to consider on many topics.

Lots of Apple as per usual with Relay FM. If you hate Apple you might want to steer clear but while I run a very mixed setup I’m quite curious about the Apple enthusiast space so it suits me fine.

Ditching Hourly

Jonathan Stark has a thing about not billing hourly. I think he has some points, especially for experienced techies there. Beyond that, this podcast repeatedly gets into your relationship with your clients. How you market, sell and execute. How you promise, negotiate, figure out what clients want and all that. There’s lots of good stuff. Unfortunately the podcast occasionally becomes very mostly a vehicle for fairly cheap questions and answers and after a while you’ve heard a lot of what he has to say. But I think the value before you hit that point is quite high. And I still check in on it.

The Business of Authority

Now this is Jonathan Stark again but now with Rachelle Moulton and better topics. So this gets into developing a business in the consulting space. I think its incredibly valuable for programmers that want to be more than just a pair of hired hands.

The Art of Product

This goes into the space of trying to start a product business and I think that’s in mind for a lot of independent developers since generally you have the skillset to do the core building. This podcast covers both that and all the other stuff that goes into running a business. I think they cover it well and they don’t overstay their welcome. Strongly recommended if you think product might be for you.

I will cut this list there and call it short and sweet. I hope this ends up useful to you. Considering they are podcasts you are likely hours away from finding out still, even if any of these speak to you. For me these sorts of podcasts have kept me good company, contributed greatly to my thinking around my business and in general been very entertaining. I hope they serve many of my readers just as well.