Freelancing Challenges, Lessons Learned, and the Future

Purple and teal birthday cake with the Scissortail logo and the number two on it, with the words "It's our birthday" and confetti and streamers next to, along with the website:
This post shares some freelancing challenges and lessons learned from the past two years, and a glimpse of what the way forward looks like.

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This week, Scissortail Creative Services, LLC, is celebrating its second birthday. Like all two-year-olds, we’ve experienced some growing pains, have come a long way, and still have a lot left to learn.

In this week’s post, I’m going to get real with you about the freelancing challenges I’ve faced over the past two years as a business owner, some lessons I’ve learned, and why I’m excited now more than ever about the future.

Freelancing Challenges

If freelancing were easy, everyone would do it, right? Freedom, flexibility, being one’s own boss . . . what’s not to love? It’s true; I love all these things. But business ownership is not all sunshine and rainbows.

Freelancing is sometimes really, really hard. Many of the things I worried about when I started my company have happened:

  • Late payments: I’ve had clients who didn’t pay me until I followed up repeatedly. This meant waiting several months before getting paid. Meanwhile, I have employees and subcontractors to pay—and of course, my own bills.
  • Scope changes: For one firm-fixed-price contract, the client changed the entire scope of the project at the very end—requiring a complete overhaul of everything we’d done. This was in spite of having approval from the client’s assigned subject matter experts at every step of the way.
  • Project delays: Some clients have pushed the beginning of their projects by several months. Others have hit the pause button midway through due to SME availability or shifting priorities. This has meant revising project plans, reallocating resources, and some serious juggling acts when everything starts going again. Freelancing is a feast-or-famine kind of gig that even our best-laid plans can’t always prepare for.
  • Personal setbacks: One downside of being your boss is that you don’t get paid sick days. Earlier this year, I had to slow down after a personal injury. This meant taking time off, saying “no” to new projects, delegating work to others, and negotiating existing timelines.

The good news is, I’ve managed to handle all these challenges—and keep my house. Of course, I had help from an amazing team! All of these challenges have been learning experiences that will help me avoid those situations in the future and grow my business.

Lessons Learned

There are three important lessons I’ve learned from the freelancing challenges I’ve experienced over the last two years of running my business.

1. Don't let a lack of confidence hold you back.

Before I started Scissortail back in 2020, I was worried that I wouldn’t be able to run a business and wouldn’t be able to get enough clients. Before I started the blog in early 2021, I worried that I wouldn’t have anything “new” or worthwhile to say. But I did these things anyway, and I’ve been successful. What I’ve found is that confidence often comes from just jumping in and getting started. If you’re confident about your ability to do something before you’ve even tried it, I’d suspect the Dunning-Kruger effect. I find a little bit of self-doubt just makes me work harder. (But perhaps that’s anxiety talking?)

2. Set very clear expectations from the beginning.

Setting expectations early on can stop problems before they start. You can set expectations in a few different ways:

  • Contracts: The most obvious way to protect oneself against things like scope changes and late payments is through contract language. Enlisting the help of a lawyer to nail down your contract language is a worthwhile investment. Be specific about what’s included in the scope and what happens if there are delays, changes, or other out-of-scope events.
  • Invoices: Besides listing the payment due date and method of payment on invoices, my lawyer advised me to also include language (mirroring the contract language) about late payment fees or early payment incentives. And I no longer wait until an invoice is past due to send a reminder.
  • Documentation of Roles & Responsibilities: Creating a “stakeholder expectations” document that you share with your client, subject matter experts, and others involved in a project can provide clarity about team members’ roles and responsibilities throughout each stage of the process. (This is a useful tip for anyone, not just freelancers.)

3. Be intentional about your direction and growth.

One of the lessons that has stuck with me the most from the eLearning Freelancer Bootcamp is about narrowing down who my ideal client is and what kind of work I want to take on. Think of this as Marie Kondo-ing your business. Picture what your ideal life looks like. What does your ideal business look like? What will you need to do to get there? What will you need to let go of?

This kind of intentionality has given me such clarity and peace of mind that even when I hit rocky times, I don’t feel stressed or worried about the future.

Especially in the past year, I’ve been able to let go of projects that don’t spark joy—such as those with clients who never pay on time. I’ve also put more thought into which projects I want to be a part of—which ones bring me joy, knowing I’m making a difference in people’s lives and in the world. And that brings me to my last point . . 

The Future

Now more than ever, I’m excited about my business and what’s in store for me and my team. As I’ve focused more on being intentional, that has meant centering myself and my business on my core values.

As a person with isolating disabilities and as an LGBTQ+ mama bear, inclusion is something I care about deeply. It seems that diversity, equity, and inclusion (DEI) topics have risen to the top of many companies’ priority lists over the last few years, but they’ve been a priority for people in marginalized communities for a lot longer—and will continue to be so.

As I’ve written about in previous posts, I’ve come to realize that we in learning and development fields have a critical role to play in shaping workplace culture. From orientation and new hire training through competency building and leadership development, we are instrumental in shaping the behaviors and attitudes of the organizations we work for. So, I believe we have a moral and ethical obligation to use that influence to help create more inclusive learning experiences and welcoming workplaces where all employees are represented, included, and valued—in short, where they feel like they belong.

To more accurately reflect these values, Scissortail will be undergoing some big changes very soon. If you’re passionate about inclusion like I am, I think you’ll be thrilled to see what we have coming up.


Here’s a recap of my three biggest lessons from Scissortail’s first two years and the freelancing challenges I’ve experienced:

  1. Don’t let a lack of confidence hold you back.
  2. Set very clear expectations from the beginning.
  3. Be intentional about your direction and growth. (Marie Kondo your business!)

Stay tuned for updates about our new direction and focus. Exciting things are in the works! I hope you’ll celebrate with us when we’re ready to launch.

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