Turn Your Skills Into Dolla Bills

I’m what people refer to as a generalist. Project management is a skill set that is replicable across all content areas and applications. That doesn’t mean I am the best fit for any project. I am most efficient and effective when designing and managing projects in areas with which I’m familiar.

Being a generalist also doesn’t mean that everything I can do is something I want to do or should do. I started working for myself to make money doing what I love, and I needed to define what that meant for me and narrow my offerings for clients to things that gave me what I needed and solved their problems. 

“Do whatever brings you to life, then. Follow your own fascinations, obsessions, and compulsions. Trust them. Create whatever causes a revolution in your heart.”
— Elizabeth Gilbert

Over time I’ve turned this process into a formula for identifying the most marketable skills that will also give someone a business model that serves the life they want to live.

What Can You Do?

Maybe you already know what you’re going to do as a freelancer. Even if that’s the case, I encourage you not to skip this step. Brainstorming everything that you can do will help you identify all of your discreet skills and skills adjacent to your areas of expertise, making you a more rounded freelancer.

Start with a list of all of the things you can do. You’re not writing a resume; you’re thinking about all of the things you know how to do that can potentially help you escape your cubicle…so think big. In addition to education, past jobs, and other training/experience, consider the following:

  • What seems easy to you that’s hard for everyone else?
  • What are you always helping people with or giving them advice on?
  • What have you become an expert on just because you were curious about it? (watched ALL the YouTube videos, read all the articles, etc…)
  • What have you become an expert on to survive? (e.g., budgeting, sewing, meal prep)?

What Should You Do?

Just because you can do something doesn’t mean you should. Let me repeat that, just because you can do something doesn’t mean you should. This differentiation is part of shifting to a boss vs. employee mindset — as a boss, you get to decide what you do based on what it gives you — joy, money, time, etc. This equation might look different at the beginning of your freelance career — you may need to take all of the work you can get in the beginning, and that’s ok — but ultimately focusing on the things that you love, in addition to what is most marketable and profitable, will make your business more sustainable long-term. Here are a few things to consider when you’re deciding what you should be doing:

What Do You Love Doing?

When you work for other people, you don’t often get to choose what you do based on what you love (or hate). When you work for yourself, you get to build a business based on doing what you love doing every day. More than anything else, this question will help you build a sustainable business that serves your life.

Here are a few questions to help you think about what you love doing:

What is your favorite kind of work?

  • What gives you energy?
  • What do you look forward to?
  • What work doesn’t feel like work?

What is your least favorite type of work?

  • What do you avoid?
  • What depletes you?

What Are You Good At?

We’re all naturally good and certain things. Go back to your list of everything you can do and think about each in terms of skill. Here are some basic labels to get you started:

  • Interested in learning: I want to know how to do this
  • Basic: I can get the job done, but I’m still learning
  • Intermediate: I’m confident in my skills
  • Advanced: I really know what I’m doing
  • Expert: I’m an expert and can lead others in the work

What you love and are good at will sometimes be the same. But you may be learning new things that you love and aren’t that great at yet. That’s fine, those things will probably just take a bit more time. The fact that they are new and challenging makes you love them. You’ll just need to think about prioritizing these things strategically so you can continue to do them but not let them eat up all of your time.

What Will Make You Money?

The first thing to consider here is the ease of getting started. If you’re ready to escape your nine-to-five right now, you need skills that are ready to go and don’t need a lot of prep or start-up funding to be viable. For each of your potential skills, figure out if you have what you need to get started right now or if you need certifications/licenses, equipment, etc. 

Using this criterion will help you get your freelancing business off the ground. It doesn’t mean you can’t build toward other skill sets later, it will just give you a quick way to get going and start building your business right away. Starting with skills that can make you money right away will also help you take the leap. Sometimes we make excuses about starting new things because the barriers are too high, if you can pick something viable to begin with, it will lower your barriers to entry.

Another criterion that will help you find the most straightforward skills to make money is whether or not you have an existing potential client base or network. When I began freelancing, I started out by doing exactly what I was doing before, I just did it as a contractor instead of an employee. I had built a reputation for quality before I went out on my own. Since most of my clients were former employers (or people they had referred me to), they knew that I could get things done and had no problem paying me a higher rate to do that if they didn’t have the overhead and responsibility of an actual employee. If you want to try something totally different, that’s fine too but, same as above, your barriers to entry and fast money in your pocket are going to be higher.

You also want to consider what skills are in demand right now in the freelance marketplace. This factor will be particularly important for trying something completely new. Do your research about what skillsets people need the most and focus your efforts there. You can do a general search about most in-demand freelance skills, and you can also get more specific as you think about your target market.


It is important to understand that to build a sustainable business that truly serves the life you want to live, you will always consider each of these criteria together. You’re not going to decide to do something just because you love it but are bad at it, because it’s pretty hard to make money off of things you’re bad at. You’re also not going to do something just because it makes money but you hate it, because if you’re going to do something you hate, you might as well go back and work for someone else. Consider how all of these criteria fit together to build profitable work that you love and reconsider the criteria again and again as you go, because your skills will inevitably change as you and your business evolve.

Ultimately it will all be put to the test when you start engaging with clients, and you’ll go back and revise again. Entrepreneurship is a journey, not a destination. You now have the freedom to change your business model as needed to align with your clients, your preferences, and your life.

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