In this episode of The Learning Pro Live, I wrapped up the week with a topic that floods my inbox more than any other: How do I transition from a full-time role to freelancing?

To answer this, I invited the incredible Ashley Chaisson to the show. With over 15 years in the industry, Ashley offers a unique perspective. She currently balances a senior eLearning developer role at Trelliant while maintaining a successful side-hustle. She is living proof that you don’t always have to choose one path over the other immediately.

If you have been toying with the idea of going out on your own, here are the key takeaways from our conversation.

The Hybrid Approach

There is a common misconception that freelancing requires a dramatic, “I quit!” moment. However, Ashley and I discussed the benefits of dipping your toe in the water first.

Ashley’s freelance journey began with a specific financial goal: paying off student debt. She started by taking on small gigs via bid sites (which she admits were terrible!) before refining her strategy. By maintaining her full-time role while building a client base on the side, she created a safety net. This “hybrid” model allows you to test the waters, build your reputation, and ensure you actually enjoy the solitary nature of freelancing before cutting the corporate cord entirely.

The Portfolio Debate: Show, Don’t Just Tell

We tackled the hot topic of portfolios. Some instructional designers argue they aren’t necessary, but Ashley and I are firmly in the “pro-portfolio” camp.

When hiring, Ashley looks for the mechanics behind the design—she wants to see how you solved a problem. I shared my own experience where simply having a website that acted as an interactive resume brought clients directly to me, eliminating the need to cold-call.

Struggling with NDAs? A common barrier is the inability to share confidential work. Our advice? Create concept pieces. Build a tabbed interaction or a gamified scenario based on a hobby or a fictional company. Clients rarely read every word of the content; they are looking at your visual design skills, your user experience (UX) understanding, and your ability to use the authoring tools.

Know Your Worth: Pricing and Taxes

Perhaps the most daunting part of freelancing is the administration. When you move away from a salary, you lose the “invisible” benefits: superannuation, paid sick leave, hardware costs, and software licences.

We discussed the importance of calculating your “real” rate. If you charge $50 an hour, you aren’t earning $50 an hour. After taxes and expenses, you might be earning less than minimum wage.

The Strategy:

• Calculate the client’s alternative: I often remind clients that running a face-to-face induction for 20 people involves venue hire, travel, printed materials, and facilitator fees—often costing upwards of $50,000 annually. When you frame your $15,000 eLearning solution against that, the value becomes clear.
• The “Double It” Rule: Ashley suggests taking your hourly equivalent from your full-time job and at least doubling it to cover your taxes, software, and rainy-day fund.

Agency vs. Direct Clients

If you are currently working in-house (perhaps in government or a corporate L&D team) and feel you lack the speed or business acumen to go solo, consider moving to an agency first.

Agency life is fast-paced. You will learn how to manage scope creep, how to estimate hours for storyboarding and development, and how to value a project commercially. It is the perfect training ground to build the confidence required to eventually negotiate your own contracts.

Just Start

Whether you want to build a “quitting fund” of six months’ savings or start moonlighting on weekends, the most important step is the first one. Connect with the community, look at what others are charging, and don’t be afraid to turn down work that doesn’t meet your value.

Watch the full interview above to hear our specific advice on handling scope creep, dealing with difficult clients, and why you should never undervalue your skillset.