5 reasons why freelancers don’t close high-ticket deals

Vanshika Mehta
8 min readAug 29, 2021


Every single new freelancer I know has a dream to become a 6-figure freelancer. Heck, even I did when I started in January 2020. I was sold on the dream that I could make a significant amount of money with the right direction and clients.

The aspirational 6-figure freelancer was going to be my reality. That’s what I kept telling myself as I started and got the wheels rolling on freelancing.

When you are on an adrenaline rush, nothing can stop you, right?

Except for one thing.

Repeated failure.

While I dreamed with glitzy eyes about being a 6-fig freelancer, I was not able to make that much money as quickly as I wanted, and I realised failing repeatedly injured my willpower.

Failures are stepping stones to success, but how many punches to the gut can one person actually take?

The reality is not too many, which is also why many people quit freelancing before they even learn what’s stopping them from closing these 6-figure deals.

Once you give up, there’s no going back.

If you persevere, you will learn.

This entire scenario got me thinking about ‘why do freelancers not close 6-figure deals’ as often as they like.

Here are what I think the contributing reasons could be.

Misplaced positioning of skills and abilities

Every one of us becomes a freelancer to do X thing. We love that X thing, and it gives us immense happiness to do X thing. However, when we begin freelancing, we are lost.

If we aren’t guided, our gut says that offer as many services as you can, and someone will bite at the bait of one of the services.

Truth is, no one wants to work with a generalist these days.

Generalists are great in jobs, but in freelancing, you have to be a specialist.

A specialist who knows one thing, and knows that one thing like their left hand. They know it so well, that you can cross-examine and cross-question, and they’d be able to fight every curveball with smartness and tact.

Becoming a specialist requires positioning yourself as one and defining your script to the T.

For example, my pitch nowadays is that I’m a brand strategist who helps startups understand their brand heart, and then using that, align the strategy of the company. Along with that, I consult on the communications that the brand should be putting out into the market to build awareness, generate revenue and build loyalty.

By being crisp and niche, I have aligned myself to the kinds of clients I want to work with; and moreover, I have defined my services so crisply that there is no second-guessing if Vanshika does this or that.

Positoning yourself in the eyes of your target market is the first step in getting found and known for X thing. The more you get known for X thing, the more demand you build for yourself. The higher the demand, the higher the price.

Specialists by default have a higher inbound lead generation rate too, since they’re known for solving X problem.

Just like with doctors; if you have a bone problem you go to an orthopaedic and if you have an eye issue, you go to an ophthalmologist. You don’t go to a general physician expecting them to help you solve your problem.


The second reason why most freelancers don’t close 6-figure deals is that they don’t invest in sales collaterals.

Blog posts — long-form articles

Case studies — success stories from your time

Landing pages —to convey your skills

Testimonials and reviews — spoken words for you

Deck — a way to timeline your achievements

As a freelancer, while you’re busy at work, all of this might seem like a task, but this task will make you money, if you invest in it wholeheartedly.

The investment does show an ROI fairly soon because all of these work as conversation points through the prospecting journey.

During the prospecting journey, clients are looking to understand:

  • Can this freelancer deliver?
  • What makes this freelancer special?
  • What am I missing if I don’t work with them?

Therefore, all of these collaterals

  • help drive conversions because of the detail involved
  • help educate your prospects on if you’re a fit for them
  • help overcome objections by self-answering their questions
  • helps strike up a conversation by turning the interactions into a learning experience
  • helps to drive conversions: The right collateral can help inspire your customers to take the leap, closing the deal and driving conversions for your business

The more you expose yourself to a prospect, the higher the chance they will convert. The more collateral you expose, the higher the chance they will trust you.

Trust can never be bought, but it can be won.


A huge reason why I do these articles is to build trust in the freelancing community and to transparently share my hits, wins, misses and losses.

Understanding the tripwire

Tripwire is a conversion tactic that convinces your prospect that you’re worth the money by biting into small commitments over time, rather than a more expensive one upfront.

A lot of the times once you have a conversation, you realise you aren’t aligned on budget. But an initial ‘no’ does not mean a big fat no to working together. There is a way. The tripwire way.

You create a low-cost alternative to an expensive product to increase immediate conversions and convince them into a further commitment.

It’s a try now, buy the whole thing later.

For example, my tripwire is a consultation call priced at $X per hour, the goal of the consultation call is to consult + not give out too much information + convince them why the 6-figure amount is worth it for them.

My goal on the call is to show them the value they’re going to get by working with me and why the price I’m asking gives them the maximum ROI they can get.

Tripwires are a tactical game more than anything. They’re meant to be dicey in the aspect that the prospect feels like they’re bombarded with value, whereas you know you’re still holding 1% back.

Market awareness

Freelancing was always competitive, and in 2021, it’s going to get more and more tricky to climb up the ladder.

Market awareness for freelancers does two things:

  1. Helps you understand your ‘market worth’
  2. Ensures you aren’t just the ‘cheapest’ in the market

When you spend time talking to other freelancers, you understand how they build their pricing stack, and how the successful ones build more than just a ‘service’ — they build a ‘highly-demanded service’. That highly demanded service helps them price above the average of the market.

The second, and a tricky one to understand is that the cheapest freelancers usually don’t last the longest. If you think you’re ‘getting clients who’re willing to pay you a rate below the market rate’ and that’s good — my friend, you are so wrong.

Burnout, my frenemy will greet you very soon

You’re doing a disservice to yourself and the entire community. You’re telling prospects that you’re willing to be exploited and also, cut your friends and community by playing with pricing.

Not a nice thing to do at all.

Talk to freelancers, understand how they built their business, take in their tips and tricks, and implement.

Being a 6-figure freelancer is not a fairytale dream, I made it happen in a handful of months.

Finally, last, but not the least


When you’re in a job, you’re forced to keep learning and upskilling. When you’re freelancing, it is not on your to-do list. You get caught up with work, and forget that you’re not meant to be within a tiny box you’ve drawn for yourself.

You have to keep stepping out of the “box” — your comfort zone, and push yourself to keep learning new things.

One thing I’ve realised is that high-quality clients always check if the freelancer is updated with the latest trends and tools. I’ve actually lost a few deals because of this myself.

Look at this. As a digital marketer you’re expected to know coding and UX design. This is real data speaking.

Let me share a personal story about Figma, an interactive, collaborative design tool used by most UI/UX designers today.

While I was at my corporate jobs, I had heard of Figma and saw others using it — I never really bothered to learn or watch or invest time in this tool.

I didn’t know how to use or even work around Figma files till up to about 4–6 months into freelancing. If I was to be a UX writer, I needed to learn this, because clients expected I know how to work with and around this tool.

When I said I wasn’t comfortable, it left a sour taste in their mouth. They presumed I should know Figma if I was into UX writing. Also, me not knowing Figma was double work for them, since now they had to copy across things from a Google Doc to Figma.

I got away with it a few times by submitting content as comments, or on a Google Doc; but then I realised this isn’t going to be a long-term solution. I needed to learn Figma — how to enter text, and not mess up the formatting. If I did, I also needed to know how to fix it. I’m not a UI designer, so mistakes were bound to happen, but the fact that I could actually work around and within Figma made a world of difference.

Nowadays, most of my UX writing projects are directly done on Figma itself and clients love it. It adds a touch of professionalism to what I do.

And, that only happened because I invested time in learning this tool.

Clients want the best quality work for their brand/deliverable

Clients know what they want, and inconveniences aren’t usually welcomed

Clients have plenty of choice amongst freelancers

Stop stagnating. Look around you and see what other freelancers are doing to one-up themselves. Ask other freelancers the smart questions so you can learn.

If you’re an introvert and don’t want to talk to people, that’s okay. That shouldn’t stop you from looking at your toolkit like an investment. An investment in yourself.

Start picking up those skills and tricks from Youtube or any other instructional website. The world is here to provide you with umpteen and more information — are you willing to take it?

Ask yourself.

Get better at your craft every day

Make your services unbeatable.

To summarize

Freelancing is all in all a game of chess. It’s not always about winning, but it also is.

In the game of chess, you’re competing to protect your queen. Do it well. Do it smartly. Do it with flair.

Don’t lose deals because of something that’s very much in your control. Everything mentioned here can be worked upon and should be — in my opinion.

There can be many more reasons why freelancers don’t close deals, and you might even disagree on these. That’s okay. This is an indicative article from my experiences.
I want you to do better, get better and be better every day.

That’s all.

If you liked what you read, reach out to me on Linkedin, and stay updated on the next Freelance Masterclass which will happen in September; 100+ people have taken the class already!



Vanshika Mehta

Founder, TFL | Building purposeful global brands in DTC and Tech | Linkedin Top Voice '21, 100K+ followers |