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Upselling for freelancers: My number one tactic for increasing revenue

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Upselling for freelancers

You are leaving money on the table in your freelance business.

You could provide more value to your clients and increase your revenue simultaneously.

But you are probably overlooking this potential.

That potential revenue stream? Upselling.

Upselling works for all involved. Your client gains more value from someone that they already trust. You increase your revenue by not having to look for more clients.

It is a win-win.

When most freelancers approach upselling, they make the mistake of not building trust first.

This is the critical component of this tactic. You need to show the value that you provide to provide more. Your client will be begging to hand you more money after you get them that first win.

The other mistake that I see freelancers make here is that they try to automate the upselling process. While I am a HUGE fan of automation, there is a time and a place. Freelancing is about networking; don’t let automation get in the way. Automation does not allow for the fineness and personalization required to make this work.

My process for upselling

  1. Build Trust
  2. Document
  3. Find Solutions
  4. Quick Wins
  5. Present

How I used upselling to turn my first project into a win

When I first started as a freelancer, my goal was to get a client. If I could prove to myself that someone would pay me money for these skills, then I could make this work. I also knew that I had a lot to learn about how to manage clients.

My first client was going to be a learning opportunity.

So I set out to find anyone that needed help with anything in regards to WordPress.

That person happened to be a chef that needed recipes entered into his WordPress site.

Not development but WordPress adjacent.

So I took it and got to work.

To build trust I completed the work 2 days ahead of schedule. When I was in there I noticed that WordPress and a bunch of plugins were out of date, a few console errors were slowing the site down, and the UX of the recipe pages were not ideal.

I updated WordPress and the plugins while I was in there entering the content.

When I went back to the client I told them about the quick win (WordPress updates) and the other opportunities to optimize his site.

He instantly hired me to do more work.

  1. I had built trust by completing the work quickly.
  2. I gave him a quick win by fixing the WordPress out-of-date issue.
  3. I presented solutions and offered a packaged deal.

How to add upselling to your freelancing strategy

I bet your wheels are already turning. You have ideas for how you can start adding this into your workflows with your clients.

Here is exactly how I go about it:

Build Trust

This is the most essential aspect of this strategy. Before you can sell additional work to your clients, you must first build trust.

This means completing the original scope on time, attending meetings, and providing regular updates. Use the initial scope to provide value and show your worth.


Next is to keep a running list of additional value you can provide. I use Notion and keep a note for each client. I write down our wins (these can be good to call out as they help build trust) and items where I could provide additional value.

Don’t run to your client now; we still have a few more steps!

Here are some examples of additional value you could provide:

Find Your Solutions

Review your list of items that you documented. Which ones are services that you can provide? Do you already have a solution in mind? Write out each problem and solution. This is also a good time to figure out how much effort these items will take to resolve.


Problem: WordPress core and plugins are out of date, which creates a vulnerability for potential security issues

Solution: Update and test WordPress’s latest version along with the latest version of installed plugins. Resolve any conflicts.

Quick Wins

This is the secret. Give your client a quick win and help build trust by taking care of one of the smaller items. Something that takes you less than 30 minutes.

Write out what the issue was and what your solution is. Then fix it.


Now, it is time to use all of the information you gathered. Inform the client of the items you found and how you could help them get solved. Present them in a problem-solution format along with a cost.

If you built trust and found actual pain points for the client, this should be a win-win for all involved.

Here is an example email:

Hey Tim,

It was great working with you on your website. I am glad I was able to help you make your landing page look better; it sounds like it is already starting to improve conversion, too!

While on your site, I noticed that WordPress core and some of the plugins were outdated. This can create future security issues; I highly suggest taking care of them.

Since WordPress is the most crucial part, I already updated to the latest version while doing the other work.

However, I would suggest getting those plugins updated and setting up and configuring automatic updates. This is something that I can do for you; it would cost an additional $500.

Let me know if you want to get this done; I know taking care of it as fast as possible is vital. I could do it early next week, say the word!

9 times out of 10, the client will ask for you to do the work. Everyone wins.

This was my secret weapon for years

I used this technique during my freelance career to bring in extra income and build trust with clients. Sometimes, it was an additional $500; sometimes, it was much more significant. Many of these clients whom I spent time building trust came back to me many times in the future. This superpower made me a lot of extra income, so I rarely had to go out looking for work.

It is easier to sell to someone who already bought from you than to someone who has no clue who you are.

Choose your upgrade

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