How To Convince Your Boss To Let You Go Freelance

If you’ve been putting together your plan for leaving your 9-to-5 job and venturing into the brave new world of freelance, there’s a potential client I bet you haven’t stopped to consider: your current employer.

When I started my freelance career, my first client was the same PR agency I’d been working for over the last two years. There were things outside of work I needed to be able to dedicate my time to but I was committed to my job and team. I loved what I was doing, but I also craved the freedom of flexibility and autonomy.

If this sounds like you, keep reading because I’m going to share my step-by-step process for convincing your boss to let you go freelance.

Pinpoint Your Value

The most important factor in convincing your current employer to let you switch from full-time to freelance is to pinpoint the unique value you bring to their business.

For me, it was my knowledge of and connections within the video game and esports industries. Beyond my expertise, my proven loyalty and track record for being a high performer also helped contribute to my cause. I had just been promoted about six months prior and worked well with my team and clients.

Once you have your unique value identified, gather important milestones you’ve hit throughout your time with the company. I like to focus on quantifiable milestones because numbers are the best way to communicate results to your boss. For my situation, this was the amount of new business I helped secure for the company, additional retainers I negotiated with existing clients, high-profile news hits I secured for product launches, etc.

Do Your Research

Freelancing is far from a new concept but nowadays more and more businesses are embracing this change in the workforce. Before you approach your boss with your freelance plan, do your research to make sure that freelancing is actually something you can afford to take on.

When you’re a freelancer, you’re forfeiting your company-provided benefits like healthcare, 401K matching, and paid vacation days. So take time to do some research and make sure that you’re ready for the change.

You also want to make sure that the jump from full-time to freelance is sustainable within the company you’re working for. Meaning to say, that you can continue to not only show your value but identify areas where you can continue to pick up additional work when projects end.

If you’re looking for more guidance on things to take into consideration before starting your freelance career, get your hands on my freelancer starter kit when you join our community.

Create A Plan

The last thing you want to do is pitch the idea of freelancing to your boss without a plan in place. You’re asking for a significant change and in order to get the best outcome, you’ll need to prove that going freelance is the best route for not only you, but your employer’s business goals.

Start by looking at the next six to twelve months and identify key moments where you regularly play a significant part in the business. For me, this was around client conferences and product launches. Once you have those key moments in place, think of the value you add to those occasions and the amount of time it typically takes to complete the necessary work-related tasks.

Freelancing is about hourly rates. Even if you negotiate a monthly retainer, you want to make sure you’re being compensated for the amount of work you agreed to for the amount of time estimated so you don’t fall back into what could feel like a 9-to-5 grind.

After you identify your value and key business moments, list the types of tasks you want to do as a freelancer to help support them. Then look at what you’ve written out to determine if it’s too little or too much work to support your freelance goals. From there, adjust where you need to and start to imagine how you’d like to bring this up to your boss.

The Pitch

Let’s recap, before you schedule a time to sit down and pitch the idea of freelancing to your boss you want to have the following:

  • A clear understanding of the unique value you bring to their business

  • Confidence through the research you’ve done that you’re ready for freelance life

  • A plan of action for how you will transition to and execute freelancing so effortlessly, they’ll hardly notice the difference

Once you have these three factors in place, ask your boss to schedule a time for a one-on-one conversation. It’s important this meeting be scheduled during a time with minimum distractions. For example, if you know your boss is particularly busy in the mornings, aim for the afternoon.

Start the conversation with confidence. This is a proposal you’re pitching, not a favor. Switching to freelance is a business-related request so don’t go into the meeting thinking that you’re going to appear weak or less-than for asking for something that you want.

Start with something like this:

“I would like to discuss the opportunity of transitioning to a freelance employee with you today. I’ve created a plan of action that I’d like to share for how I can continue to add value to your business in this new capacity. I enjoy working with you and hope this is something you will take into consideration.”

This messaging is clear, to-the-point and friendly. From here, share your plan and ask for feedback along the way.

Be prepared to answer questions like:

  • Why do you want to switch to freelance?

  • What hourly rate are you expecting?

  • How many hours a week can you commit to?

  • Are you willing to come into the office?

  • How long do you want to freelance for?

Every individual’s answers will be different so it’s important to think of what you want from the setup. Be prepared for where you’re willing to compromise and where you are firm. Having clear answers will make the decision-making process much easier for you and your boss.


AUDREY ADAIR IS THE FOUNDER OF ‘THE SCOPE’ AND A GLOBAL FREELANCE COMMUNICATIONS PROFESSIONAL. SHE STARTED ‘THE SCOPE’ TO PROVIDE RESOURCES AND COMMUNITY TO FREELANCERS AND THE SELF-EMPLOYED. CONNECT WITH AUDREY ON INSTAGRAM, YOUTUBE AND LINKEDIN.