Stepping Out into Freelancing with Confidence

Stepping Out into Freelancing with Confidence

Two exercises to help you get out of your own way

Let's talk about getting started with freelancing...

It's an age-old story, one many of us are familiar with. Goes a little bit like this...

You want to start freelancing, but you just can't get yourself to take the first step. It seems like you'll be begging people to pay attention to you. There's no chance anyone will trust you with their website, their business, heck, even some graphics or video they needed edited. Who are you to ask them for MONEY?!

This is the biggest hurdle I hear from people who have never freelanced before, especially those who have never started a business or considered themselves "entrepreneurial". We can call it a lot of things, but it starts with a belief that "little ol' me" isn't worth being valued to do work for someone else.

Take a deep breath. You've got this.

I have been on both sides of this conversation many times, and the most important thing you need to know about business owners is they don't want to do any work they don't have to do.

They don't have the time.

And it goes deeper. If I own a business and I'm working hard, I definitely don't want to take precious time to TRY to do anything I'm not COMFORTABLE doing. Especially if I'm actively making money doing the things I'm good at. Like the actual function of the business. The haircuts, the massages, the therapy. I'd rather be doing that.

This is why people hire contractors: like accountants and plumbers... and web developers.

You want to be that hired contractor and people need you to be that contractor.

So let's go through a couple exercises:

  1. Let's put you in the shoes of someone who might be looking for a simple website for their business. Let's get in their heads. That's job #1.

  2. Let's talk about how to craft a post that talks directly to that person and makes them want to trust you with the work they don't want to do AND pay you well for it.

Hopefully, with a little noodling on these two exercises... you'll learn to get out of your own way.

I should note, I'm not the end all and be all of freelancing. I'm relatively good at talking about myself and what I'm doing, and have about 7 years experience in business marketing and communications. I have freelanced before. I also am a white, cis, queer woman, so I have some implicit privileges that might make this easier for me than others. If you find a better way to find clients or these tips don't vibe with you, by all means, ignore me!

Ok let's gooooo!

Exercise #1 - Put your feet in their shoes. Get inside their heads.

Imagine this. You have a successful side hustle as an artist. You make beautiful little clay pots and your local business is pretty popular at the local craft fairs around the holidays. However, you keep getting suggestions to sell your pots online. Your friends and customers think you could have a year-round business with an online shop. The pressure is real, but you don't want to live that #etsylife. You want your own website.


You hate computers and you don't know where to start. Posting about upcoming shows on instagram is the extent of your ability. All you want is to magically have an online shop, where everything works and you don't have to think about anything but how to upload pics of new work, and where to send the orders.

You know you need a website...yesterday. Maybe you know someone who can help? Maybe you'll ask on Facebook...


Let's take a step back.

This person is:

a) Not interested in learning new tech to build their business.

b) Super busy already and wants to fast forward to having a web-based way to sell more products.

c) Doesn't want to even TRY to do the work you can already easily do.

I would see this person as an "Ideal Client". I don't want to work with someone who will be all up in the code, giving me their opinions, but I do want someone who has a clear website plan and goals so I can hit the ground running.

It can be helpful to think about what type of client you would like to attract. Ask yourself some questions:

  • Do you want to work with a sole proprietor, like our distracted side hustling potter above?
  • Do you want to work with a bigger business, which might want to be more collaborative in the site design?
  • Do you have a passion for a specific topic and want to work with businesses related to that?
  • Do you need to prioritize making more money over being choosy with which clients you attract?

Tip: If you are building an example portfolio from scratch, make practice sites for the types of businesses you'd like to work with, e.g. if you are a foodie, build a restaurant site.

Defining an ideal client can be tough, and as the last question here implies, maybe you don't have that luxury if you need to make some cash quickly. Being able to choose an ideal client is definitely a privilege.

If you really need a client right now, imagine you are the person who needs to hire a contractor to do something they don't want or can't afford (time-wise) to do themselves.

What is their main motivation? Their time is worth more to them than their money.

Show them how you will help them keep their precious time, as long as they part with a little of their (not as precious) money.

And then they will magically have the website they were dreaming of!

Exercise #2 - Leading a horse to water a.k.a what you post matters

I won't sit here and try to convince you that I am a master of persuasion. I'm not. However, I have learned some skills in confidence and telling potential clients exactly what they need to hear to make an informed decision.

Let's break this down with the text of a Facebook post I made earlier this week asking random friends I've collected on that site since dinosaurs ruled the earth if they would like to hire me to build a website for them.

Here is a screenshot of the post.

Screen Shot of Facebook Freelancing Post

The opening establishes trust, tells the truth, but doesn't tell the reader EVERYTHING.

"For the last two months I've been brushing up my front-end web development skills. Pretty exciting stuff! And, hey, I'm not too bad at it. ;)"

Yes, I have been brushing up on my front-end web dev skills for two months: TRUE. Yes, it is exciting: TRUE. Yes, I am good at it. A little self deprecating, but that's my style: TRUE.

What I didn't say: I am in a 30-week full-stack web dev bootcamp and I've been learning as part of that. I could have said this but positioning myself as a student erodes a little trust. I have edited websites before, but I haven't done most of front-end web dev before: Not worth saying.

I'm currently looking for small businesses or individuals who need a new website or need to add mobile responsiveness or accessibility features to an outdated website (a legal concern, now that the US gov has passed new ADA guidelines for websites!)

This paragraph gives me a chance to say who my ideal client is. I want to work with small businesses or individuals. Primarily because I think these folx can make a decision quickly (I am on a deadline, but they don't know that!) and also because individuals tend to run into less red tape with decision making.

I also added the line about the ADA guidelines to add a sense of urgency, which can drive the person reading your post to take action. Do know that adding that sense of urgency is not always necessary and sometimes can be done in a way that makes people feel manipulated or icky. I only added this here because I feel accessible websites are important and I know some people reading my post will say to themselves "Wait, what?" and maybe learn something. I'm a teacher at heart.

If that's you, I'd love to talk. If you have someone you'd like to refer me to (even if it's just a business whose website you HATE) please send me a DM. Location doesn't matter. I work remotely. I'm not doing this for free, but I am pretty affordable.

That's the pitch. It's soft. I'm not demanding anything, but I am asking readers to take action. I say "If you are my ideal client... please contact me." I also say, "If you know my ideal client... refer me." I set some parameters, because the audience I can reach on Facebook spans the continent, if not the globe. And I make sure people know I am asking them to pay me, but not sell their first child to do so.

(An aside about "affordable.": I think we could spend all day discussing if that helps or hurts. You could say it sets me up to make less money than I could make. I included it to make my post approachable. Since no-code products are very accessible now, I want people to know they can afford to pay someone to build them a website, they don't have to DIY. It's a fine edge, and it can cut both ways.)

P.S. I linked my website here with more info (and as an example). It's pretty simple, but if you've got something fancy in mind, don't worry: almost anything is possible.

Finally, I share the link to my portfolio and note that it's an example of my work, but not the breadth of my capability. I think this is important. Most people I know would not be able to create my portfolio from scratch and it helps to establish trust. If potential clients click through and know they want something like that, they are sold. If they know they want that plus a shop, or another integration, they can extrapolate that I'm good for it.

I would never have shared this post without a portfolio that showed some decent representation of skill. It would have been a futile effort.

So to review, my post does four things:

  1. Establishes trust.
  2. Draws in the "right" readers - hopefully some ideal clients.
  3. Makes an ask or a call to action.
  4. Shows proof of work.

As you are going out into the world and looking for freelancing clients, on Facebook or elsewhere (because, let's be real, the heyday of Facebook has passed), remember to think through these steps.

Now it's your turn.

Write your own outreach post and try to communicate the above points.

Now, read it back over...

  • Does your post show why you should be trusted?

  • Are you talking to the people and businesses you actually want to work with?

  • Did you actually ask for something? Was your request clear?

  • Are you showing them what you are capable of through a portfolio or example site?

All this comes back to confidence. You don't have to be 100% confident on the inside. You don't even have to 100% on the outside. However, you do have to sound confident when you offer a service to others.

People can smell uncertainty and self-doubt. If you are feeling either way, make sure you have a friend check your post before you send it. An extra set of eyes and a gentle reminder of how cool you are can make a huge difference.

Now get out there, write some awesome posts, find some wonderful clients, and start freelancing!!

People need your skills and your unique approach to web development. Businesses need accessible websites and updated designs. The world of freelancing is your oyster. Don't sell yourself short.

Please reach out if you have any follow up questions--good luck!