Hit Subscribe Freelancer Q&A

Hit Subscribe Freelancer Q&A

We’re publishing the freelancer Q&A series as a podcast. Hope you enjoy!

Episodes

August 4, 2026 20 mins

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Another podcast taking on ideas for services niche. In this installment, I look at the idea of creating automation systems to spare enterprise developers and/or quality assurance folks from toil.

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  • Jim Collins' classic business framework for what separates truly great companies from merely good ones is explored in...
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"Info products" are things like podcast courses or eBooks that anyone with an internet connection can create and sell pretty easily. Can you make a living selling these types of products to software engineers?

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This one hits close to home for me.  A reader/viewer wondered if helping companies make strategic decisions about codebases is a good niche, and I can answer this because it was once kind of my niche. 

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As a freelancer and service provider, you'll likely offer value during your sales and onboarding process.  But when should you stop?  When should you charge for things to show your clients that your work is valuable?

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Long ago, when I was blogging more regularly about identifying niches, a reader asked me how I found mine. While I don't do a ton of exposition content, I thought this topic might be interesting for viewers.

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If you're offering services as a freelancer, does it make sense to unbundle strategy from labor? This episode digs into that question.

This podcast is courtesy of Hit Subscribe. Prefer to watch the video version of this podcast? View this podcast as a video, here!

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If you have a single big client, engaging your services for an unspecified amount of time, it can be easy to fall into an employee-employer style relationship. How can you avoid that?

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For a while, I was getting a lot of questions about whether something would be a good niche for indies. In this video, I answer the question of whether improving code performance is a good niche.

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You may hear the terms "niche" and "positioning" tossed around a lot, often interchangeably. What do these really mean, and what's the difference?

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February 11, 2026 23 mins

Maybe you're currently employed or between jobs. But it occurs to you that you want to go off on your own and start consulting (as opposed to freelancing with labor services). How do you do that?

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Plenty of employees entertain the idea of going freelance. But one of the biggest barriers to entry is the perceived risk of doing so. Is there a way to jump to freelancing with minimal risk?

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In this installment, a question submitter wonders whether it would be better to earn promotions into leadership before leaving the salaried world, or whether to leave as an individual contributor. Which is the right path?

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Occasionally, you might find yourself with a whale client, or at least a profitable one, that treats you poorly and shows no trust in you. How should you handle this?

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Occasionally, you might find yourself with a whale client, or at least a profitable one, that treats you poorly and shows no trust in you. How should you handle this?

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Sometimes a client is looking for labor and expects you to bundle in the strategic piece. For instance, they expect architecture to come along with a software development project. How to handle this?

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Depending on fate to bring you business can lead to gaps between projects. How do you setup some kind of sales funnel and get leads into it to avoid these gaps?

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You're collaborating with your client on a time-sensitive deadline and you get sick.  How should you handle that?  Whose problem is it, ultimately?

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You've got a full-time job but want to go indie, and you line up your first contract. How do you think about how much runway you need to create between current savings and that first contract, for when it expires?

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Links of the week:

  • A post from Sawmills, which introduces log parsing, explains its importance for transforming unstructured logs into actionable data a...
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If you've built an audience on a platform other than your own website, how do you go about turning that following into a marketing funnel for something you're offering?

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It will sometimes come up that a prospect or client asks you to implement something that's either too vague to work or a flat-out bad idea. What should you do in this situation?

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