4 Things Successful Freelancers Do

4 Things Successful Freelancers Do: A TLDC Event Recap. Young African-American woman smiling while working on a laptop outside a cafe. scissortailcs.com

Share This Post

Reading Time: 6 minutes


If you’re new to freelancing or you’ve been thinking about freelancing, you’ll want to check out this post for four things successful freelancers do.

In this recap of TLDC’s “Exploring Freelancing” event from Friday, February 25, I break down four key takeaways and provide a list of resources shared throughout the day. Although the audience for the event was learning and development (L&D) professionals, these tips are universal for any freelancer.

Be sure to watch TLDC’s website for the recordings when they become available. I’ll also update this post with the links.

Okay, let’s get to it!

1. Make Authentic Connections

Two closely related themes came up again and again throughout the entire day were authenticity and relationships.

Andrea McEneaney shared some down-to-earth advice about how to communicate with clients in a way that balances professionalism with authenticity—even sharing text messages with clients that demonstrate that balance. She encouraged us not to be afraid of being ourselves with clients. That’s how we make connections! She also emphasized the importance of regular check-ins to keep things transparent and on track, saying that frequent updates foster connection and trust.

Life is all about people.

In my session, I discussed how relationships are important for getting—and keeping—clients. They’re how we get referrals and repeat business. Both my session and Andrea’s offered tips for keeping in touch with clients after the project ends. For example, Andrea said we can “make them jealous” by telling them about a cool project we’re working on that we think they’d like.

Star Peterson offered practical advice for networking, making meaningful connections, and building your experience. They emphasized the importance of being genuine, rather than participating in shallow networking activities that are more like checking a box.

If you’re not sure how or where to make connections in the L&D field, be sure to catch the recording of Star’s presentation. They also shared a number of resources that are included at the end of this post.

Do something you love and you care about. Share your enthusiasm with other people, and the networking will just come naturally.

2. Set Realistic Expectations

Before deciding on a freelancing career, make sure your expectations are realistic.

Joseph Suarez’s session focused on the “LinkedIn” version of freelancing versus reality. He mentioned that many people may have the idea that when you freelance, you’re completely “free” to work however and wherever we want. It’s right there in the name, right?

Theoretically, we could work from the beach—if we didn’t care about things like screen glare and sand getting into our computer. But more likely, we’ll end up as Joe did, working from our hotel room while staring longingly at the ocean through the window.

The reality is, even though we’re technically “the boss,” we’re not always fully in charge. We have to adjust to things like client delays, unexpected changes, and other hiccups that inevitably happen. As freelancers, we have to be comfortable with a certain level of ambiguity.

Likewise, if something goes wrong, the boss is the one who has to deal with it. As Joe put it, being the boss is both a pro and a con.

In the freelance life, you're always on the hook. The buck always stops with you.

We also have to manage expectations around our workload. If you want to work a 40-hour work week, don’t schedule 40 hours of client work—or even 35. You will spend a good portion of your time working on things like marketing, contracts, accounting, professional development, business development, and of course, project management. 

Lisa Crockett shared that she spends about half her time actually doing the work, with another 30 percent or so spent meeting about the work.

To manage expectations, set boundaries for yourself AND your clients. Some examples are:

  • Choosing when you’ll work
  • Limiting evening and weekend work
  • Scheduling vacation time and taking sick days
  • Controlling scope creep

3. Specialize

Lisa talked about the importance of knowing what your version of success looks like, rather than comparing yourself to other people’s versions of success. If what you really want is to do what you love and earn enough to pay your bills, then it doesn’t matter if you’re not making gazillions or working with Google.

Whatever makes you happy—that's your version of success.

Along those same lines, Dr. Parker A. Grant presented a session on finding your niche. He encouraged us to list things we really love doing; then list things we’re really good at, and finally, combine the lists. That’s our “niche zone.” For example, if you love art and you’re good at explaining things, maybe you could specialize in creating infographics or animated videos.

Lisa reminded us of four questions Tim Slade asked in a recent TLDC presentation:

  • What am I good at doing?
  • What do I enjoy doing?
  • What do I want to be hired to do?
  • What are people willing to pay me to do?

These questions are based on a Japanese concept known as ikigai, and you can see a graphic example of it on the “Who We Are” page of this website.

The beautiful thing about freelancing is that we can specialize in a particular area. If you really LOVE needs analysis, that could be your niche. You don’t necessarily also have to do development. This is where those relationships come in—maybe you could partner with an instructional designer or eLearning developer who hates doing needs analysis.

4. Plan for the Practical Stuff

Lisa and Joe both discussed practical concerns that freelancers need to plan for, including the questions below. I encourage you to watch the recordings of their sessions for more information on these.

  • How much money do you need to make?
  • What are the start-up costs?
  • How much will you need in savings to get started?
  • When and how will you get paid?
  • How will you manage your finances?
  • How should you set up your contracts?
  • What kind of computer will you need?
  • What software will you need?
  • Which work samples can you share?

It’s also important to know how much work you can handle at once. Several of the day’s speakers mentioned a “sweet spot” of about three projects at a time. Of course, the number of projects you can reasonably take on depends on the complexity of those projects, as well as your availability and previous commitments.

Another practical consideration is having a portfolio. This is particularly important for instructional designers, eLearning developers, and learning experience designers. A portfolio provides evidence of your skills and helps potential clients trust that you can really do what you say you can do. 

Lisa provided some practical advice for getting experience if you need it. Also refer to this past post about how to get experience for your portfolio.


To recap, here are the four things all successful freelancers do:

  • Make authentic connections
  • Set realistic expectations
  • Specialize
  • Plan for the practical stuff

In addition, Joe shared that successful freelancers are self-deterministic, handle ambiguity well, and are able to pivot on short notice. 

If you’re not sure you’d enjoy freelancing—or that you’re cut out for it—try dipping a toe in by taking some side jobs (provided that’s okay with your employer). That way, you can see how well you like it and whether it suits you before quitting your day job.

Good luck with your freelancing journey!

Questions? Leave a comment below.


The following resources were shared throughout the event. Some of these resources are free, and others are not. 

Presentations and Handouts

Speakers' Websites

Finding Work

Finding Volunteer Opportunities

Communities and Groups

Professional Development


As an Amazon Affiliate, I earn a very small amount if you choose to purchase books from the links below. This does not affect the price you pay and helps to support this blog.

Creative Stock Assets

Business Management Tools

Building a Portfolio

Building Your Own PC

Asking for Referrals

More To Explore

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Thanks for subscribing!

We promise not to spam you!