The Inner Work of Starting a Freelance Business

How you feel about your work and its place in your life is a huge deal. Before you can build a freelance career that’s both rewarding and exciting, you have to do the internal work of understanding yourself—your boundaries, your needs, and your motivations. When you first , this self-reflection is the most critical step.

To help people figure this out, I rely on three core tools: personality tests, the concept of ‘I’ versus ‘T’-shaped professionals, and a straightforward skills audit.

Using Personality Tests for Clarity

While I don’t think personality tests are a magic solution, they can offer some valuable self-awareness. Think of them as a snapshot of your current mindset. One of the most useful frameworks I've found is Edgar H. Schein’s work on career anchors. He identified eight anchors that point to your core values, needs, and skills. They work on a sliding scale, so you can see where you land on each one.

For anyone looking to build a , three of these anchors are especially telling:

1. : If you score high here, you’re driven by the desire to build your own thing. Success, for you, is measured by the enterprise you create.
2. : A low score suggests you’re comfortable with the inherent insecurity of freelance life. You're less likely to be emotionally rocked by the ups and downs.
3. : A high score means you deeply value the freedom to define your work on your own terms, which is a classic freelancer trait.

The beauty of Schein’s method is that there are no right or wrong answers; it simply describes who you are. Armed with that knowledge, you can build a career that aligns with your natural inclinations.

Are You an ‘I’ or a ‘T’?

The second tool helps you understand your professional shape. Traditionally, freelancing was the domain of ‘I’-shaped people—technical specialists hired for their deep expertise in one specific area. Think of photographers, graphic designers, or architects. They deliver a single, specialized service. If the vertical line of the ‘I’ represents your experience, it starts short. This creates a classic catch-22: you can’t get the job without experience, but you can’t get experience without the job. New ‘I’-shaped freelancers often get their start with assistant roles or by taking on smaller clients to build their portfolios.

While ‘I’-shaped work is still common, there's a growing need for a different kind of professional: the ‘T’-shaped person. These freelancers have deep expertise in one area (the vertical bar of the ‘T’) but also possess the broad ability to collaborate across different disciplines (the horizontal bar). A film producer is a perfect example. They don't need to know how to operate the camera, but they need to understand the camera operator’s needs and how they fit into the bigger picture. They are the enablers, the translators who connect all the ‘I’-shaped experts.

For ‘T’-shaped people, it can sometimes be harder to explain their value, as they can seem like a jack-of-all-trades. But their true strength lies in seeing the whole picture and making everything work together. Reflecting on whether you’re an ‘I’ or a ‘T’ helps you find work that plays to your strengths and helps define your .

Conducting a Personal Skills Audit

The final tool is a simple skills audit, which helps you map out where you are and where you want to go. The idea is to focus on improving your weaker areas, even though our natural tendency is to get better at what we’re already good at.

The process breaks your skills into three types: (industry-specific), (transferable, like communication), and (hobbies, languages, etc.). You can audit them in five steps:

1. List about 15 skills that are important for your current work.
2. Visualize your ideal work in 3-5 years and list the 15 skills required for it.
3. Rate your ability for every skill on both lists on a scale from 0 (no ability) to 4 (expert).
4. : Ask a trusted colleague who knows your work to rate you using the same scale, without seeing your scores. People often value skills in us that we take for granted.
5. : Compare your ratings with your reviewer’s. The discrepancies are the interesting parts—areas where you might not see yourself clearly. Use this to create an action plan to develop the skills you need.

This audit is a living document you can revisit as you grow in your career, especially when that demands continuous learning.

What About a Portfolio Career?

If your skills audit reveals a wide range of disparate experiences, you might be suited for a portfolio career. This isn’t just about applying one skill to different markets (like a photographer who shoots weddings and products). A true portfolio career involves being hired by different clients for your different areas of expertise. For example, I work as a line producer, a university trainer, and a strategic consultant. This approach keeps things interesting but also means more work to market each distinct service you offer.

Defining Your Own Success

Success is deeply personal. It’s not about comparing your journey to someone else’s. For a long time, I measured it by status and income, but now, success means doing work I enjoy while being present for my family. Take a moment to define what success means to you, separate from outside expectations. This definition will become your compass.

Of course, practical considerations like your location, the hours you can commit, or personal circumstances will shape your path. Be honest about these realities from the start so you can build them into your plan for your .

Building Your Personal Brand

After all this internal reflection, it’s time to think about how you present yourself to the world. Building a personal brand can feel daunting, but it’s really just about articulating your core values. You are intertwined with the services you sell. Your values signal to potential clients who you are and what you stand for.

Start by thinking about the brands you already love and trust. What words do you associate with them? Chances are, those brands share some of your own values. Review those words, add others that are important to you, and then select the six that best represent you and your work. These six words are the foundation of your brand. They are how you explain what you do and why it matters, helping you connect with clients who are the right fit. It’s the starting point for all .

By pulling together your identity, your skills, and your values, you can finally create a clear and concise answer to the question, “What do I do?” You’ll know what you offer and be ready to find the people who need it.