99 Problems (but a boss ain’t one)

I teamed up with Michelle Pratt from Dive Deeper Development to create the podcast that solves your freelance problems, one at a time.

Check out the episodes below or search for “99 Problems (but a boss ain’t one)” on your preferred podcasting platform. We’d love to hear from you, so say hello and share your problems or tips using the hashtag #FreelanceSOS.


The very first instalment of 99 Problems (but a boss ain't one). We introduce ourselves, explain why we created the podcast and let you know what to expect in upcoming episodes.

Problem 1: Imposter Syndrome

Ever felt like a fraud? We have. In this episode we explore Imposter Syndrome, the impact it has and how to overcome it.

Problem 2: Getting Clients

Finding clients is obviously quite important for most freelance businesses, but it can be tricky if you're just starting out (or even if you're an experienced freelancer). We look at why it's hard and what you can do about it!

Problem 3: Deciding What to Charge

In this episode we look at why it can be so scary to ask for money, and how to work out what to charge for your client services or products. We also include some tips on getting into the right mindset so you're charging the correct value.

Problem 4: Procrastination

As freelancers we're obviously all sitting around watching Netflix in our pyjamas most of the time instead of doing work 😉 So what can we do about it? As always, we delve into both practical and mindset tips to help solve this common freelance problem.

Problem 5: Isolation

Being freelance can be lonely, so how do you overcome that isolation? In this episode, we look at why we need a human connection and what actions can help if you're feeling a bit isolated.

Problem 6: Failure

Is there such a thing as failure? In this episode we look at why we're so afraid to fail, why we should celebrate "failure" and why nobody cares about your Barry Manilow t-shirt.

Problem 7: Underselling yourself

In this episode we chat about why you are doing customers a disservice when you undersell yourself, how to protect your value and why it's probably all your parents' fault (just joking, Dad).

Problem 8: Motivation

What is motivation? In this episode we look at why it can be hard to find if you're a freelancer, the counter-intuitive way to get it back, and the proper way to pronounce Mihaly Csikszentmihalyi.

Problem 9: “Bad” Clients

In this episode we talk about whether there's such a thing as a "bad" client, how some people always seem to end up with nightmare clients, and why hiding in your email inbox isn't the answer.