How Can You Go from Employed to Freelancing with Low Risk?

How Can You Go from Employed to Freelancing with Low Risk?

Author: Erik Dietrich January 23, 2026 Duration: 24:06
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? Join us to learn more. View this podcast as a video on YouTube. Links of the week: CSuite Content published a practical guide to Gen-Z slang for business leaders. Enov8 shared a clear explainer on SAP data masking. InfluxData put together a getting-started guide to MQTT. Unusual Ventures is an early-stage venture capital firm focused on technical founders. Careflow is a referral management platform for healthcare organizations. Tricentis offers Oracle App Testing for teams running Oracle E-Business Suite.

Erik Dietrich hosts Hit Subscribe Freelancer Q&A, a podcast that pulls back the curtain on the practical realities of running your own business. This isn't about abstract theory or motivational speeches; it's a grounded, question-and-answer format built directly from the challenges freelancers and solo entrepreneurs face every day. Each episode dives into specific, tactical concerns-from setting rates and negotiating contracts to managing client relationships and finding a sustainable workflow. You'll hear straightforward advice and thoughtful discussions that stem from real-world experience, offering a sense of clarity and camaraderie for anyone navigating the sometimes isolating world of self-employment. Tune in for honest conversations that cut through the noise, providing actionable insights whether you're just starting out or looking to refine an established practice. This podcast serves as a reliable resource, transforming common freelancing puzzles into manageable steps forward.
Author: Language: English Episodes: 98

Hit Subscribe Freelancer Q&A
Podcast Episodes
How Do You Quit a Gig or Fire a Client? [not-audio_url] [/not-audio_url]

Duration: 18:55
Sometimes it just isn't working out, and it's not you -- it's them. When you decide you have to part ways with a client, how do you go about doing that? Picks: Need a proxy? Check out this list of free HTTPs & Socks prox…
What Software Do You Need for Your Freelance Practice? [not-audio_url] [/not-audio_url]

Duration: 20:07
What pieces of software do you need in order to start out as a freelancer? CRM? Accounting Software? Etc? I take you through the ones that I would recommend in this video. Link Picks; Test environments: Everything you ne…
Should I Start a Business Bank Account to Freelance? [not-audio_url] [/not-audio_url]

Duration: 19:32
In this edition of the freelancer Q&A series, I take on the subject of whether or not you should start a business bank account in order to freelance. I think you ought to, and I'll tell you why, and what else I think you…
What Motivates Companies to Hire Freelancers Instead of Employees? [not-audio_url] [/not-audio_url]

Duration: 19:14
If you're a freelancer, you may be tempted to apply to job openings looking for employees so that you can convince them to hire you instead. Is that a good idea? And, more generally, why do companies hire freelancers ver…
Should a Freelancer Maintain a Portfolio? [not-audio_url] [/not-audio_url]

Duration: 17:16
A lot of people will tell you that, as a freelancer, you should create and maintain a portfolio that you can show to prospects. But is that really good advice? Link Picks Local development with PostgreSQL containers Ente…
What Should You Title Yourself on LinkedIn or in Business Cards? [not-audio_url] [/not-audio_url]

Duration: 16:17
As a freelancer, it might not be clear what kind of title to give yourself in "official" venues, like LinkedIn or on business cards. What should you put there to best represent yourself? Link Picks: A developer’s guide t…
Building a Python Training Business, with Reuven Lerner [not-audio_url] [/not-audio_url]

Duration: 1:06:18
This time around in our community speaker series, we talked to Reuven Lerner about starting a Python training business. Hear about how he got into tech, into training, into business for himself, and, eventually into a sp…
Should Freelancers Give Talks as a Way to Generate Business? [not-audio_url] [/not-audio_url]

Duration: 14:49
Someone in our community asked whether it was worth it for freelancers to gain recognition by giving conference workshops or online workshops. I generalized this to the subject of "should you give talks as a freelancer t…
Is Freelancing a Lateral Career Move? [not-audio_url] [/not-audio_url]

Duration: 13:27
There are a lot of factors to consider when leaving a salaried job to go off on your own. One of the perhaps lesser considered ones is what, exactly, does this mean for your career. Is starting to freelance a lateral car…