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As a new freelancer, I had to adjust to a new world. Trust me it is, in fact, a whole new world and I’m not speaking in Aladdin terms. Just like anything in life, there is a learning curve. Thanks to ambition, a strong motivation to develop an alternative income stream and my Leo-ness, I raced up the curve faster than light.

Here are a few mistakes I made along the way that I would like to share so your journey will have a rather useful map (and not the confusing paper kind).


As an employee, you are probably used to representing your company. Whether it is meetings or selling services to potential customers, you have a brand reputation to lean on. But as a freelancer, things are a bit different, a lot different actually. In this world, you are marketing yourself, your expertise and your experience. It takes some effort to think through and then promote that image, offering a freelance service. What else does it take? Vulnerability. So it makes sense that it is a big kick in the guts when a client says no to your proposal or worse, you send out over 20 proposals and get zero response.

I recall going through an existential crisis at the start of my freelance journey – Am I not as amazing as I thought? Are there millions out there better than me at this project that fits my skills so perfectly? The reality is that most of the time, it has nothing to do with you. So get ready for rejection or even non-acknowledgment, loads of it and just keep it moving. Think about it as breadcrumbs leading you to the right projects.


I know! I know! You are just excited to get started. You’ll take anything at this point but I wouldn’t be having your back if I didn’t let you in on a fundamental point. Don’t say Yes to Every Single client and here are a few reasons why:

  • You are too busy working on other projects

  • The compensation is substantially below the time you’re going to spend to execute

  • The client is rude, disrespectful or unresponsive

  • The client just does not pay

Experienced freelancers stay away from sticky freelance projects because they’ve learned the ropes and catch red flags quickly. One of the best strategies is to set some boundaries:

  • Get on the phone with your client to get a sense of if they are positive or not

  • Agree the number of version modifications the contract allows

  • Set up milestone payments – it’s dangerous to get paid at the end

  • Restrict access to documents until you release final versions if you can


The fight for potential clients is so intense that when you get the projects, there will be a tendency to overextend yourself. A wise person once said, “Underpromise and Overdeliver”. Somehow, we forget that in the excitement of finally getting the hang of freelancing. Taking on too many projects at a time or agreeing to unrealistic deadlines is a terrible idea.

I have been here many times and to be honest, I still get locked into the overpromising conundrum. Many all-nighters later, I have learned to say no because the “Yes” freelancer is stuck with:

  • A client that doesn’t pay on time or all

  • Losing out on potentially great clients while working on bad contracts

  • Your quality of work suffering

  • Disappointing your client

  • Getting a bad reputation


When I started freelancing, my focus was on PowerPoint presentations because I find it extremely relaxing and get to express my creative inner-artist. I learned very quickly that many people can create presentations, a lot of clients would prefer an actual graphic designer. Most importantly, I could earn way more doing something I am very skilled at; an area that has a limited pool of experienced freelancers. I’ve found that I now enjoy it much more than I thought. The fact is, passion for what you do is great, but don’t forget why you are freelancing. If for you, it is about earning additional income, then stay the course.

Besides the income, I found that focusing on a specific niche really catapulted my freelance journey. Instead of trying to sell all the services I could execute for clients, I focused on marketing a specific offering: “Want financial projections, valuations or business plans? Then I am the freelancer for you.” Simple. Some of the key benefits of focusing were that:

  • I built a portfolio of clients in my niche

  • I developed so many of the same kinds of deliverables that each became a template for the next

  • I figured out ways to improve the client experience beyond the typical project delivery

  • I learned what my potential clients wanted to hear and converted them quickly

  • I became more confident in pitching for and winning over clients


Perhaps it was the inexperience of selling myself as an actual business or my uncertainty about whether people were looking for what I had to offer – I was a bit shy in my early days. What I learned very quickly is, again, it is not about me. Everything is about the client.

So think about that when you are sending out proposals. Focus on:

  • How you can help the client work through their problems

  • Getting your clients talking and sharing as much information as you can get

  • Making your client comfortable with you as a person

  • Connecting with your client

If all else fails, just take each call as practice. Remember that Practice Makes Perfect, so the more calls you have, the better you will get at it. Kapish?

These are just a few of my mistakes and trust me there are more. So do not be afraid to fail at this freelancing thing because as I have come to believe; ‘Failure is Feedback’.




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