Five lessons learned in my first five weeks of full-time freelancing


(I can’t really say no to a ridiculous alliteration.)

Holy crap, guys. This week marks the seventh (!) week that I’ve been running my own little business full time. Sometimes, it feels like I’ve been doing this forever, and at other times, I feel like a super-n00b who knows absolutely nothing. But isn’t that always the way?

One of the big benefits of working for yourself is that you learn a lot, and you learn it really, really quickly. Self-employment is a bit of an emotional rollercoaster ride, because suddenly you have to figure out all sorts of things that never crossed your mind before, and there’s no boss to give you advice or tell you what you should be doing. Instead, there’s a whole Internet of advice out there… much of it contradictory and confusing.

That being said, reading about other people’s experiences can be really helpful as well, especially for people who are thinking about pursuing full-time self-employment and haven’t yet taken the leap. I know that when I was thinking about it, reading about other people’s experiences was both interesting and comforting.

On that note, without further ado…

1. (Almost) everyone is a little flaky. It’s probably not personal.

I have learned that a lot of people don’t do exactly what they say they’ll do, when they say they’ll do it. In the past few weeks, I’ve had to chase a lot of people around for a lot of things. Gently prodding and reminding has become a part of my regular routine.

In the beginning of my freelancing career, especially when I was working full time and freelancing on the side, this would drive me crazy. What was wrong with these people? Why didn‘t they care about the work I was doing for them? Why did they hate me?!

However, as a full time freelancer, I’ve started to realize that in most cases, it’s really not personal. Amazingly, other people have lives too, and are busy doing their jobs, running their businesses, and attending to all sorts of things at their end. A project of theirs that takes up a bunch of my time might not be their top priority. Things slip through the cracks, and it mostly has nothing to do with me (a crazy concept, right?). I know this for a fact because I’ve had the occasional email or two slip through the cracks of my own inbox, and I’ve inadvertently been the flaky one with other people. Whoops.

Lesson: Most people are a little flaky occasionally, and it’s best to be at peace with that. However, truly flaky people totally suck and are a waste of time.

2. There will always be people who think I’m too expensive.

Ahhh, yes, pricing. Everyone’s favourite topic!

Over the years, my rates have changed quite a bit, and at every single stage, there have been people who tell me that I’m charging too much, or that they can’t afford me. The interesting part is that this can happen no matter how high or low your prices are, because different people have wildly different expectations. I’m totally okay with this, because I know that there are people who are both cheaper and more expensive than I am, and that there always will be, no matter how much or how little I charge, so I don’t let this get me down.

Lesson: I’m perfectly happy to not being the cheapest option, because I know that I’m providing a ton of value to my clients. Repeat after me, fellow creatives: I’m not not a commodity.

3. And then there will always be people who think I’m a bargain

Yes, this definitely goes the other way as well. I’ve had several moments where I realized I was undervaluing myself. Whoops!

In creating a quote for any individualized service (like, say, a custom website), it’s important to keep in mind not only the level of client (e.g. Is this for a small business or a large corporation?), but the actual value of the product that you’ll be delivering. Will your product or service help your client earn hundreds of dollars? Thousands of dollars? More? How about saving them time and energy? How about bringing them comfort and happiness, which can’t be measured but are still valuable?

Lesson: This stuff’s complicated, but not completely impossible to figure out.

4.Things that seem easy to me won’t necessarily seem easy to clients

This is a huge lesson, and it’s one that I keep having to tell myself over and over again.

It’s my natural tendency to talk about work like it’s no big deal, partially because I’m a bit modest by nature, and partially because I’ve been building up my skills for years, and a number of things come easy (or easier) to me at this point. However, I’ve come to realize that this does me no favours. Even though lots of aspects of my job seem easy or obvious to us, they clearly aren’t to most of the world — that’s why people hire us. It’s important to remember that.

After all, for clients to value the work that we do, we have to value it too! I’ve learned that it’s really important to walk my clients through my process so they know exactly why every decision has been made. This has the benefit of having clients become a part of the process, and it also helps to demonstrate that I’m a problem solver and a strategic thinker, and not just a decorator or a mindless worker drone.

Lesson: Perception is really, really important, guys. And we’re (mostly) in control of how others perceive us. So it’s time to stop diminishing our knowledge and skills just because certain things seem easy or obvious to us.

5. Hoarding knowledge is no substitute for actually taking action

You can read all the articles in the world about freelancing, running your own business, finding clients, and so on. When you passively absorb knowledge over a long period of time, it’s really easy to feel like that’s enough. You’ve got this! But let me tell you… actually putting this great advice into practice feels completely different.

Oh, trust me, I thought I was pretty ready because I’d read and read and read everything I thought I’d need to know. And this did really help me a bunch, so it definitely wasn’t in vain. But did it remove the fear of quitting my job, landing my first clients, and feeling like I’m making my whole business up as I go along? No, no it did not. So, if you’re an overthinker who lives inside your head (like I tend to be), know that knowledge, while helpful, can only go so far.

Lesson: Start taking action. Preferably now. Experience is a much better teacher than anyone or anything else!

P.S. Special thanks to Michelle Ward, my amazeballs career coach, who suggested that all of these lessons I’ve been learning might make a good blog post!

21 thoughts on “Five lessons learned in my first five weeks of full-time freelancing

  1. Could not agree with you more on lesson 1 that truly flaky people just suck and are a waste of time (hopefully I have not been one of these people). This used to realllllllly irritate me as well, but I’m learning to freak out less knowing I now have to do it routinely if I want all the facts. Hope your first 7 weeks have been good! So excited to be working with you!

    • Oh man, actually flaky people are the worst. THE WORST. But luckily, most people I know don’t fall into that category so all’s well (…so far, haha). I’m excited to be working with you too :D

  2. Really well-written post, and it’s helpful to get a little insight as to what it’s like on your end. These can also apply to almost anyone who’s self-employed, particularly those in a creative field. I’ll keep these in mind as I continue to dip my toes further into the freelancing world. :)

    • Thanks, Cassie! You’re right, these probably can apply to any self-employed person, or even someone who’s running a small business with a few employees. I’m looking forward to hearing about your journey into the crazy world of freelancing, and if you ever wanna chat about freelancey things, lemme know!

  3. Well written! And so very true! I am starting my own journey on this self-employment route and I am terrified – but reading things like this makes me breathe a little easier. Thanks Dara! :)

  4. Dara: Great post! I like the 5-5 list format a lot, and the generosity of all the information. I can relate to SO MUCH of this.

    I like #4, though I find myself often with the opposite tension — that what *seems* easy to my clients if often not easy for me. I’m thinking about facilitating writing groups, answering emails and being available generally when people come early to class, want me to quickly look over their work, etc. I LOVE doing this, but I’ve had to work hard to set boundaries around it (and communicated them gently) so that I don’t burn out. Since I’m open and friendly and casual, all that stuff seems like it’s easy to do, more like a friend hanging out than like someone in a pretty intense job.

    Interesting to compare notes. Thanks for the great post. I’m so glad that you are following your passion and busting out of the 9-5!

    • Hey Chris! Thanks for your comment, and I’m glad you enjoyed the post!

      It’s interesting to hear your perspective on having the opposite tension, because now that you say that, I can completely relate to that as well. “Easy” tasks can often be really time consuming — especially those requiring interaction with people, which can be really rewarding, but also draining (which I think, for me, is part of the introversion thing). It’s all a crazy balancing act!

  5. Really fantastic post and tips! I try not to worry to much about flakiness, because I know I can be sometimes too. And the modesty thing for sure! :)
    xoxo Aimee

  6. I will definitely keep this in mind when I take the step into freelancing full-time! One question though… how do you find clients? I wouldn’t mind freelancing in the evenings, but can’t for the life of me figure out how to get clients consistently. I’m sure it would help if I had my portfolio online, so maybe that’s it. I’m always curious though if designers actually approach perspective clients and ask for work or if people just find you somehow.

    • Hi Jennifer,

      That’s a really good question and I’m sure that every freelancer has a different answer!
      As for me, I’ve found clients through a combination of word of mouth (past bosses, clients, friends, etc, bring up my name when someone they know is looking for something I can do) as well as being active online and talking to people. For example, sometimes I’ve seen people tweet about needing a developer so I’ll tweet them back and sometimes a project comes of it! I haven’t approached clients myself, though I’m sure others do. Different things work for different people and all that!

  7. Great list, thank you! I especially like number 1. I hadn’t quite made the distinction between “they hate you” and “they just over-committed to this project.”

    • Haha! At this point I just try to assume that most negative behaviour isn’t personal — much better for one’s sanity/self-esteem!

  8. Great post! Although I’m not a freelancer, I can relate some way
    I agree with Chris with the client thinking it is easy when it’s not actually for my part especially the whole concept making. Some clients will say “I want it to be shiny, classic” or something like that. Some people expect you to have something in mind already. Thinking of something that they might love is hard for a first-timer on such things or I’m not that creative hahaha

  9. Dara,
    Congratulations on taking the leap into the freelance world! That is awesome! It looks like you are already making a lot of discoveries about yourself (and others). I’d love to hear your updated perspective in 10 weeks:)

    • Thanks, Andrea :D I’ll definitely be posting more thoughts down the road since my brain is chock full of ’em. I hope you’re doing well and enjoying the awesome Toronto weather we’re having now!

  10. All five lessons are spot on. I am especially dwelling on the potential difference in the perception of value between myself and my clients. Thanks Dara and all the best.

  11. Loved the article! I’ve used most of the freelance sites on the internet, and they all have their pros and cons. I think the best one I’ve used is Its easy to get paid and really easy to find work without needing a different cover letter for every job application. Worth trying out if you haven’t already :)

  12. I loved this article. It’s REALLY nice to hear some REAL experiences with launching (and living) a small business! I’m in the process of launching my own graphic and web design studio with plans to go full time within the next few years. I can’t wait to experience all of the things you’ve written about in this post! I hope you keep writing articles like this :) Thanks so much Dara!

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.