Things I’m Learning the Hard Way

It’s been about two months since I returned to freelance after two years of working with Chartbeat, and these last two months have been, well, hard.

I’ve done full-time freelance before, but it wasn’t nearly this much of a struggle. Back then I was 25, and I didn’t care very much about building a long term sustainable business. I was mostly motivated by working in sweatpants, and telling myself I was so liberated because I didn’t have a “real job,” and hey no one can tie ME down! It also probably helped that the other times I’ve freelanced I’ve been lucky enough to work with incredible agencies such as Happy Cog, SimpleBits, or MetaLab, so I always had a big group of better people backing me up and cushioning me from the realities of running a design business.

This time around things are more of a struggle, and the stakes feel higher. I’ve had to ask myself daily why I need run my own small humble little business when it’s so much easier not to. At Chartbeat life was GOOD you guys. I had cool opportunities to work on fun products I believed in. I loved my coworkers – some of the best smartest weirdest funniest people I’ve ever met are there. I had a flexible schedule, unlimited vacation, unlimited coffee, and creative freedom. (Oh god, why DID I leave again? By the way, Chartbeat is hiring, if any of this sounds appealing to you!)

As I have to remind myself sometimes hourly, I left because I want to build something myself, even if it is just a tiny little one woman plus one cat design studio. I had to move on so I could keep learning, so I could keep being uncomfortable and growing as a result. I had to, as Cheryl Strayed says, “walk into the darkest woods without a stick.” It’s a thing we all have to do sometimes, and it was time for me to do it.

In keeping with the dark woods metaphor for a bit – I have already tripped, and been bitten by hostile animals, and gotten lost once or twice. But every day I learn my way a little better, and it gets a little easier.

I’ve been thinking about the mistakes I’ve made so far, and what I can take away from them, and how I could be better than I am. So tonight I sat down with a glass of wine (or three) and wrote down the output of that thinking. Initially I didn’t intend to publish this, but since my last post on this site was “hey, I got a job at Chartbeat!”, I thought perhaps it was time for an update. And maybe the things I’m learning about carving out a path here in the scary world of freelance life will help other people trying to make their way.

So. Here are a few guidelines I’ve learned so far; the things I believe but struggle to live and therefore feel compelled to write down.

Yet another heap of words about client communication

Clients really really want someone that’s going to talk to them. Even if the news is bad: deadlines have slipped a little, I have ideas that are unfinished and I don’t feel great about yet, I don’t agree with their choices; I have to talk to them about it. Like, way more than feels natural to me. I have to send updates morning and night, or anytime I have a productive thought about the project. For the record, this is the hardest thing for me. Rather than admitting I’m struggling to find a solution, or asking a dumb question, or saying “I think you’re wrong,” I’d really prefer to resolve the issue myself, or avoid the question, or just prove they’re wrong with my stellar designs that blow their dumb criticisms out of the water (this never, ever works).

When I DO talk about a pain point, or ask a lot of questions, or disagree, clients are usually PUMPED. Because most of the time, just knowing that I’m getting worked up about their ideas and their needs is enough to make them happy. They are usually suffering for their work, and they want to know I’m suffering right along with them – that I give a lot of shits about how their thing turns out.

As an aside, some clients aren’t really suffering over HOW their project turns out, just when. I’ve had people tell me I don’t have to make it THAT good, and I don’t have to really love the work, I just have to get it done quickly. That’s fair, but these are not really the projects I want to work on. I want to feel proud of the work, not proud of how quickly we rushed something out the door. Part of the assumption in hiring someone with my skills and experience is that I can work fast, but I care way more about doing thoughtful work than cranking out a ton of projects back to back, even if it means less cash coming in.

But I still have to work as fast as I can

Having said that, working as efficiently as possible is obviously an important thing which I will struggle to be better at forever. What I’ve learned so far is that working efficiently has a lot to do with NOT trying to create stellar designs that will blow them out of the water. Working efficiently often means just sitting with your fingers on the keys and compelling them to start making terrible ideas and having faith that with more communication and more terrible ideas, it will become something good.

It has so much to do with those impossible calls and emails and meetings where I ask every dumb question and listen hard to every annoying bit of input. It has something to do with setting a timer and telling myself, “in 20 minutes, I will have made one part of this, regardless of how terrible it is.” And doing that about 20 more times. And then checking in with the client.

The other other hardest thing is being vulnerable; I have to show unfinished work and continue to ask probing questions about the product and be receptive to feedback and new ideas. It’s about communication, but it’s also about humility. I won’t get it right the first time, and I’ll always need input and productive conversations to get there. I have to talk to clients about my ideas and my progress and the things that I don’t know yet, even if my ego-fueled desire to only show perfect work or have all the answers makes that so hard.

The opposite side of this coin is having the confidence to disagree, to make a case for the more useable approach, to care enough and be brave enough to compel everyone involved to do it right. I can’t be be afraid of seeming rude or disagreeable just because I think there’s a better solution than the one the client is proposing. This is the thing they hired me for. But when I disagree, I must do so with a spirit of humility, and with the knowledge that everyone wants to make the best thing for their users. Unless I discover they don’t want to make the best thing, or simply can’t. Then sometimes I have to fire them, but I try to do so with kindness.

I have to think about communication and efficiency and humility and confidence all the time. Thinking about and enacting these qualities is harder than any other work I do, but it’s also the most rewarding.

Estimates and deadlines and expectations and disappointments

One of the hardest things for me is knowing how long a project is going to take. Or that’s not true, I know how long a project will take because it will always take at least 1.2 times longer than the absolute most amount of time I can imagine spending on it (thank you, Jackie Balzer, for this very helpful guideline.)

Why do deadlines slip? Why do I often feel rushed? Sometimes it’s because the right solution requires an excruciating amount of work and garbage and meetings before it comes along, and in the early optimistic proposal phase I assume it will just happen naturally because I am a gifted genius. Then when I sit down to do the work, I am reminded again that I am not a gifted genius. None of the work comes as easy as I hope it will, it is always going to be a struggle.

There are days when things take longer than I want because I’m flawed and hungover or scared of failing or really into Mad Men right now, and this makes me feel worse until it’s all I can do to just open Photoshop and start dragging shapes around until something emerges.

Sometimes projects take longer than I want because I didn’t listen to my instincts when they told me this project wasn’t a good fit for me. How do I find out if a project is a good fit for me? How do I get better at estimating the time something will take? I ask a lot of questions before putting together an estimate, but I can’t really ask the questions that will REALLY determine how long a project will take, such as:

  1. Do you have a secret crazy boss that you’re going to unleash on me later in the process when it’s too late to get out, who will derail everything we’ve made and force us to start over?
  2. Do you think you know what you want, but once you see what you thought you wanted, will you realize it’s not right, not at all, and will this send us on a long, tedious path to redesigning the same pages for weeks on end? Will this make me cry and think it’s my fault I can’t give you this vague amorphous “feels right” thing?
  3. Do you harbor secret dreams of being a designer, and actually see me as a prop to execute your inner design diva wishes because your dumb manager wouldn’t let you just design it yourself and also you don’t really know Photoshop?
  4. Will you tell me you want “simple, lightweight” interactions, but really mean you want an animated exploding map that draws itself and then scatters across the page like smoke that slowly clears to reveal your restaurant hours?
  5. Are you really just hiring me because you want someone to sit on the phone and listen to you talk about how creative you are, and what your company could be doing if only people listened to you? Are you hiring me to be your work girlfriend because you’re lonely and bored and do I think I have to listen to you because you’re paying me hourly?

These things can and have happened to some degree, and they’ve derailed deadlines and caused me to shove my computer under the couch cushion and walk away from it because even thinking about what’s waiting when I open the lid makes me feel crazy.

One of the most important thing I’ve learned is I have to get better at saying no. No to 5th or 6th round of revisions. No to bending the terms laid out in my contract. No to people who send ideas they made in Sketch and just want me to “clean up a bit.” No to the unproductive calls that go on for hours.

I think it’s especially hard for a woman to say “no” in this industry / society / existence. I should just be grateful to be here, right? Who am I to say what’s acceptable? I have to constantly remind myself I deserve to say no, and I don’t have to always be “nice.” I do have to communicate and try my hardest, but I don’t have to run myself ragged in an effort to do anything other than tell a client no.

The truth is, being a freelancer means being thrown into a crazy shitstorm that I have little understanding of until I’m in it. Every team and every project has its own internal bizarre issues and infighting and expectations that don’t come up in the initial getting-to-know-you meetings. I have to figure out how to navigate these strange waters I’m thrown into with each new project. Sometimes that takes awhile. Usually about 1.2 times longer than I thought it would.

Again, this just means I have to think hard every day about empathizing with clients and communicating clearly and listening better and managing expectations and being honest with myself and others. These are things I’d have to think about anyway to become a good human, but freelancing compels me to work harder at being good than I previously thought I could.

Subcontracting and seductive product managers and that time I realized I’m not really a front end developer

Here are some stories about subcontracting.

The first time I hired a subcontractor was because I took on a project with an unreasonable deadline. I knew it was unreasonable from the beginning, but I desperately wanted to do it anyway because it just sounded SO COOL. Here’s a tip: smooth talking Product Managers who spend all their time talking to investors are REALLY GOOD at making you believe their startup is going to be the NEW BEST THING that you’ll wish you’d gotten in on.

So, since I knew the workload was crazy from the beginning, I hired my awesome friend Andrew Witherspoon to pitch in with parts of it. He is an amazing designer and did a fantastic job producing great work, as he always does, but nothing either of us did was right for the client. There were so many stakeholders, and nobody could agree, and we did 9 revisions on the “about us” page, and after weeks of trying with only a few pages completed, I had to fire the client. Or they fired me. Or we had to agree that they weren’t ready to finish their project, and I wasn’t ready to provide them with infinite ideas for an indeterminate amount of time and no money.

I didn’t get paid for this project (except for the tiny initial deposit, which I let them negotiate down to almost nothing because I thought this project was SO COOL), but I still had to pay my friend who worked really hard on making great ideas. Had this been the right project, we would’ve seriously kicked some ass together.

So I ended up losing money in the end, and feeling like a pretty huge dummy. But I gained some pretty valuable insights into the importance of trusting my instincts, not getting seduced by seemingly glamorous work, and also asking better questions up front before blindly jumping into something. I also learned that under the right conditions, with the right person, subcontracting could theoretically be a great way to get things done.

So on another recent project, I tried working with a subcontractor again. I should back up a bit and talk about my skills and the things I think I am good at: I used to call myself a front-end developer because I can do some pretty awesome things with HTML and CSS, and I prefer designing in the browser, and reading about responsive design makes me giddy.

But the more actual front-end devs I work with, the more I realize the value of people who specialize in this type of work. I also finally accepted that I have no interest in being one of them. I am a designer who knows enough about markup to execute most of her ideas directly in the medium where they will live (the browser). But when you get down to building production ready, super optimized, crazy interactive, multi-device ready code, that is just not my jam.

I finally admitted this to myself on a recent project after spending two days trying to make a flawless complex touch activated responsive menu that ended with me weeping into some jQuery mobile documentation, with about 32 Stack Overflow tabs open in Chrome. The following day I was bemoaning my struggles to my friend Brian Mcallister, an ACTUAL front end dev, and he agreed to take some of this work off my plate.

Hot damn. I mean HOT DAMN you guys! He got the project into git, set up Sass, gave me a thorough tutorial on what I needed to know to work within his framework, rebuilt my crappy navigation, and knocked out every other somewhat daunting interactive element I needed in a day.

Why had I made myself miserable over work that I could not and did not want to do, and wasted so much of my own time and money (I’m working on a flat rate for this project, so every hour cuts into my net hourly rate), when I could just hire an expert to knock it out in no time? This probably sounds pretty obvious to most of you, but it was a crazy epiphany for me. THIS IS HOW BUSINESS WORKS. You can hire people to do the things you aren’t good at!

How business works

I don’t know a lot about how business works. It’s the hardest part for me after communicating enough and estimating the project scope accurately. Honestly, just about everything but making designs is hard for me, and even that is a struggle – it’s just the part of the struggle I really enjoy. I have 95% of an English Lit degree and 10 years of experience working in all kinds of situations, and I have an earnest desire to make good work and build a web design studio that’s known for integrity and ingenuity. I hope that and my commitment to consistently getting better is enough to make this work.

There’s so much more I’m thinking about and learning that I could and will share, but I’m already asking a lot of you if you’ve read this far. I also really want to hear from you, person who is maybe reading this. What have you learned about running your own freelance business? What are your favorite articles and tools and techniques for solving these problems we face? I realize this is a huge topic and most of what I’ve discussed here has already been written about ad infinitum, but I’m fine with that because it’s hard work and talking about it makes it easier for all of us. So talk to me.

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40 thoughts on “Things I’m Learning the Hard Way

  • Awesome post! I’m a dev that want to have my own business again, but last time I didn’t got the balls to say no to people. So that’s going to be the first thing I need to learn.

    Good to read other have had that problem and other similar experience.

    Keep it up!

  • Thanks for sharing. I recognize all of these struggles and pain points, sadly 🙁
    One thing I’ve learned from working solo, is that I should be selling value & results, never my time. This ties into how I propose, estimate, bill and ultimately, which projects I take on.

    I could go on at length about this, but instead, I’ll just refer to the guy that made me realize a lot of this: I cannot recommend Brennan Dunn’s material enough, esp. his books Double Your Freelancing Rate and The Blueprint. Check out — hope it’ll do for you what it did for me 🙂

    Best of luck, and congrats on your business!

  • Thank you so much for this candid, humble, and honest post. I can relate to almost all of your failures and struggles (minus the girlfriend one), so you’re certainly not alone in your experiences.

    I’ve been freelancing for close to 9 years and am just now beginning to grow the freelancing gig into an actual business. One of the most important things I can share on the subject is that you absolutely, positively, no ifs and or buts, must be very very very selective about who you choose to work with. Hiring a designer isn’t like hiring a plumber to fix your drain. It’s an extremely collaborative process (I would go as far to say it’s a partnership) where you have to learn the ins and outs of your clients business, goals, mindset, way of thinking, etc. Working with a bad client can rob you of your passion, drive, time, and money, so choose wisely and be on the lookout for red flags from the outset. Unfortunately I made this mistake far too often when I got started and fell into a multi-year slump where I totally lost my passion for my work and it turned into just a job. Thankfully I’ve fine-tuned my senses over the years and am much more aware of red flags at the outset, and have been blessed to work with a handful of amazing clients as of late.

    Keep truckin’ and don’t let the negative experiences get you down. It’s all a part of the growth process.

  • This was such a great article, Meagan. Thanks for writing it.

    I recently stepped away from my own design business for the time being, taking an in-house contract position for a corporation. One thing that I had struggled with was the subcontracting aspect that you mentioned. I often had a lot of trouble finding good, reliable subcontractors that I could lean on and that also wouldn’t eat up most of my budget. I tended to try to do everything myself which was leading to time-intensive, unprofitable, lackluster projects. I realized that this is not how a business should work. In order to grow I had to be able to offload a good amount of work to “employees” or else I was looking at a future of late nights, stressful deadlines and eventual burn out.

    Of course, hiring subcontractors or employees is a whole different thing from being a one-man shop and comes with lots of pros and cons. It was the way forward but I wasn’t sure it was a step I was ready to take at this point.

  • Megan,
    Thank you so much for being flat-out honest. That list of questions that would really determine how long a project would take was so spot-on.
    I wish I had advice based on my experiences, but for many of the reasons you talked about here, I just never put all the pieces together and after a year of freelancing went back to a full-time position.
    I do know that Andy Clarke has some great episodes on his podcast Unfinished Business. I have also heard the book Design is a Job by Mike Monteiro is quite good, though I haven’t read it myself.

    Seriously, thank you for writing this. It means a lot when people who’s work you respect are fully candid about what they are struggling with.

  • That’s got to be one of the most enjoyable posts I’ve read in a while. Your honesty is refreshing!

    By the way, is mind reading one of your other skills? Because I think you just read mine 😉 Thanks for sharing what we are all thinking and experiencing.

  • Great share Meagan, thank you. I can honestly say that i was at most of the points you were back in my freelance days and i kind of envy that as opposed to me, you unearthed the holy grail successfully: keep evaluating what you do and get better at it. Don’t buy into the bullshit people sell you about sacrifice when hard work means nothing unless you spend some time to make sure you’re working smarter. Yes, you will make your mistakes, everybody needs to have their own to grow, no matter how many smart books exist out there that pretend to be able to prevent them. But you want to make those mistakes once, and that it is a big step along the way.

    In relation to saying no, you want to read this piece by Andy Rutledge, it explains in detail how to say no through adequate pricing, and Andy himself is one of my main influencers on professionalism and a treasure trove for those seeking insights about it:

  • Even having been a freelancer for several years now, I still feel some of those struggles that came about on Day 1 of Freelancerdom. Recently I relocated to Seattle from a small community in Eastern Washington that was quite extraordinary in the “heart” department. The other freelancers, meetup groupies, and coworking space members really became my work family. The move prompted me to feel all those bits of loneliness I felt when I first started freelancing years ago, alongside a general, “What the heck am I doing with myself these days?” type of life question.

    With 3 other people at similar points in their lives – big dreams for our path in business – we started a weekly group to coach each other through challenges. There’s no real leader, we all take turns asking for advice and providing help. Voila! Our co-coaching group was born. We have guests every now and then to mix it up, but we limit the group size so we can stay casual and dynamic. It’s been amazing! I’d encourage you to try it out sometime, it sounds like you have a great network of people to pull into a c0-coaching group. We’d love to have you as a guest sometime if you’d like to see how it works.

    Thanks for the post, I love hearing these stories. It somehow makes my frustrations easier to bear knowing that EVERYONE else goes through the same. Luck to you!

  • Comment by Rubi
    April 19, 2014

    Sooo, I’m glad you’re doing the freelancing thing as your main gig. I think you’re doing the right thing, I think I’m headed that way myself. With the few years I had managing design and publishing projects I must say that fully vetting projects and establishing some sort of formula/spec for accepting work is key. Being over zealous is dangerous. My previous boss would often promise completed books (concept toncompletion) in just DAYS when 1-the client was fucking nuts, 2-thought they were some untapped design prodigy which I knew nothing about and 3-revisions revision revisions sucked the enjoyment out of the project. Be tough and be honest. You’ll do a better job and best of all that satisfied client with refer another and you’ll be set. Ps-I think we should work together 😉

  • Thank you so much for sharing, Meagan! I learnt a lot from your post, things I’ll keep in mind whenever I decide to work freelance.

  • It’s eye-opening for lots of young (and old) designers out there to see how someone (you) who is SO GOOD at this still struggles with the business and productivity side of things. Thank you for sharing this. I’ve been on my own for 8 years and have had to kill more SO COOL projects than I care to admit. When you get into work-for-hire, non-competes, non-disclosures, and so on, you eventually find that most of your great work belongs to someone else. So it makes it all the more important that you find others to help you, so that you can find the time to take on those oh-so-rare side, personal, or startup projects that do allow you to flex your design muscles.

    I’ll be at Smashing Conf in NYC, looking forward to hearing from you. If you’re up for it, I would love to buy you a coffee (or three glasses of wine) and share some things I’ve learned along the way. Always up for helping a fellow designer who is just now realizing how much work we really have to do.

  • So happy to see you diving back into your own endeavors and sharing this stuff, Meagan. I’ve learned a ton about some of these same times, and my CPA and I like to share them on our podcast, The Businessology Show (

    Also, happy to share anything I can with you (tips, rates, contracts, etc). You’ve got my info; call/DM/Skype anytime.

  • Comment by Tony
    April 22, 2014

    Since my “freelancing” experience consisted of putting up a “Will Web for Food” sign when I couldn’t find work I don’t have personal experience on that end. But what I do know about is the cluster of an IT department we have at work. Theybare contractors. They were hired to “modernize” one of our database systems. But someone had the bright idea they could work on other stuff too. So instead of contractors on a fixed price job they became hourly contracted employees trying to fill their time while we figure out what “modernization means. For 3 years now. Most of the original contractors are gone, partly because they were bored, partly because as a contractor, when they move on to their next gig, their resume is going to have a three year gap of “I got paid to play Minesweeper while the client tried to figure out what they wanted.”

  • Comment by Foxinni
    April 22, 2014

    Great post. I share most if not all of these issues in freelancing.

    I’ve been doing it on/off for a few years and the leasons dont come easy. As a aslo front end desinger you can easily realise that a simple design becomes infinitly complicated once you have cross browser-cross device specs to deal with. A real passion killer if you have to fix problems you created tourself!

    My main tips: 1. Charge High! You are better than most. If your results are good your client will feel like he spent his money well. 2. Never take on a job in despiration. Being desperate will impair your judgement when having to say no. 3. Dont take shortcuts, take time to build up a framework so that you are confident in what you can deliver.

    Good luck!

  • Comment by Kiki R.
    April 22, 2014

    I have been hired to execute some fantabulous marketing strategies only to find that what the client really wanted was a friend. I’m sure they don’t really think of it that way, but if you want to have lunch every day and it’s more important to you than giving me time to complete the work – then…that’s what you want. A friend. Not a marketing strategist. And of course those clients are always the kind of people you really *don’t* want to be friends with. I have also hired people to help me meet deadlines and been caught out paying them when the project fell apart. It’s tough to write those checks when you yourself will have to do without. Maybe someone else could not pay their subcontractors so they could take a paycheck in that situation – but I couldn’t live with myself if I did that. I agree with one of the other commenters – I’ve been in business for ten years and I started out loving it and now I just feel a sense of dread when I need to go to my desk. I’ve decided that (for the moment) that dread is less than what it might be going back to a “real job” so for now I am continuing and trying to find new clients/outlets for my work. Other learnings: when someone negotiates you down on a proposal they will do that throughout the project; “Yes” on a new proposal either comes right away or not at all; “Do you have ten minutes to talk?” from a person who is forever considering hiring you is just a chance for them to get your knowledge for free. This often comes from potential clients you really like/would work for. If anyone has tips on managing that – I’d love to hear them!

  • Great article. I can definitely empathize having been full-time freelance for 6+ years, then in 2013 taking a job as a creative director at a web design company, only to leave 2 months ago (Feb 2014) for the “uncomfortable” freelance world again.

    I actually wrote a self-reflecting essay about “being uncomfortable” back in 2010 for a colleague’s blog ( I feel like you literally wrote about my life, which is comforting to know considering a talented, well-known designer such as yourself struggles with this as well.

    Walking the fence between being a creative and a business person is tough. I’ve seen talented designers fail because of it. However, I have confidence that you will be fine. Best of luck, Meagan.

  • Comment by Barbara
    April 22, 2014

    I just started full time freelancing as well and I agree with everything you said here. Sometimes it’s really hard, but I think the benefits outweigh the hard stuff. I’m definitely learning a lot. Good luck to you!

  • OMG. This is sooooo me (too) 🙂 Seriously… I could have written this down. Not as good as you, but all of it I could relate to my own situation.

    Thank you for writing this and sharing your experiences. I really thought that I was one of those few that are struggeling with all of this and cerrtainly didn’t expect a seasoned web designer like you struggeling and making the same mistakes, or no better actually…. learning it the hard way too, like I and other not so experienced freelance web designers do.

  • Thanks for writing such a detailed and honest reflection. I just started UX freelancing about 3 weeks ago with a similar humble and maybe lofty dream of running a one-woman design shop that can soon turn into a couple+a cat design shop. So far I have only put up a website and talked to 4 clients (didn’t land 3, waiting to hear back from one.) It has been very hard, and your post makes me realize what I struggle is common, and there are a lot more struggles that I will experience later.

    Well, good luck to the both of us, and would love to hear more about your experience, lessons, tips, and of course I will share mine as soon as I set up a blog. 🙂

  • Great post, it made me realize that I should take out the “front-end developer” title even if I can write a little bit of Javascript and HTML/ CSS. It’s not easy figuring out titles in this shifting landscape. I’m sure you’re new venture will do wonderfully. Best of luck with it.

  • Hi Meagan, thank you for sharing this great article. I think the most maddening thing about a lot of these points is that they will somehow manage to happen again and again until you finally start to beat them down at first sight. 🙂 That’s been my experience, anyway. It helps me to listen to this podcast episode every few months: — One of the things I’ve learned is to approach client communication as a negotiation, whether before, during, or after the project. I believe this is most beneficial to both clients and freelancers.

    Now that I wrote that it feels ridiculous to be a commenter offering more advice. Anyway! Do whatever you want but please don’t give up. You’ll get better at it and it kicks FTE’s butt. We freelancers need more people like you around.

  • This was amazing! I laughed my way through it, I can relate to almost every single thing you mentioned. It reminded me a lot to this video: . My experience is that usually clients change their mind a lot, but very few are willing to recognize it so they turn it around and make it seem like you didn’t get it right in the first place. It can be very frustrating, but at the end of the day I’d MUCH rather do freelancing over working on a full time job, no doubt about it!

  • Great post, thank you for sharing. I could actually hear your true voice coming through your writing, or at least some woman’s voice. In any way I found it comforting. I freelanced for 8 years. I had corporate clients, agencies and start-ups in my mix. I can’t tell you the amount of mistakes, personal and professional sacrifices, and highs and lows I endured in my “solo” time. I’d do it ALL over again if I could, except I’d value myself higher, charge more for my talents and learn to better negotiate because still, at the end of the day, no matter what level of personal growth we get from our work, we still need to make money, save for vacations, upgrade our equipment, pay into a retirement account and so on. Still with all of that, the advice I’d give anyone stepping in to a world by themselves, is to be sure you can still laugh about it, close the door at the end of the day and have someone you can bounce creative ideas off of. Good luck to you and thanks for sharing!

  • Thanks for putting this out there. I’ve never freelanced, though I’ve thought about it. This is really helpful.

    Also, +1 on the recommendations for Brennan Dunn’s stuff and Mime Monteiro’s book. Both are very good.

  • Comment by Sunyen
    April 26, 2014

    I think does helps speed up development time substantially for me recently. Not so much replacing Photoshop or Sketch but speed up between mock ups and working htmls. This helps lowering my stress level tremendously when coping with deadlines.

  • “But when you get down to building production ready, super optimized, crazy interactive, multi-device ready code, that is just not my jam.”

    I know what you mean … this is tricky. I know I have a lot of room to grow in this area. It is a challenging, energy-requiring, problem-solve-heavy thing. And sometimes I end up feeling like the time and energy I need to use to grow in this area are busy with the challenging, energy-requiring, problem-solve-heavy aspects of actually MANAGING the project/client. And this thing tends to takes precedence.

    But for various reasons I sometimes find it difficult to want to get help from others on the stuff that might be the most fun for me if there was any of me left to tackle it. Can I duplicate myself?

  • Comment by Dan Humphries
    April 28, 2014

    Thanks for this, it was such a brilliant read!
    I’ve been thinking about freelancing for a while now and your post has really highlighted so many things that I hadn’t even thought about. I hope everything goes well for you in the future and I look forward to reading more about your adventures in the freelance world. Good Luck!

  • Glad to have you back blogging again Meagan <3 Best of luck with your freelance business, I hope everything goes well for you from here onwards!

  • Comment by Anna Aks
    April 30, 2014

    Oh… Thank you very much for your post. I also worked for three years at a place that became my family but in my opinion you can’t improve unless you step out of your comfort zone. So here I am at the same place, starting my own business and learning from the same mistakes. Thank you very much for your honesty. And to answer you question, what helps me is the various free courses on Sometimes I learn about creativity, sometimes about leadership and now I take a marketing course. It makes me feel more confident with my decisions. I wish you good luck and I admire you for not being afraid to take risks!

  • Thanks so much for writing this, Meagan. Seriously.

    I just jumped into my first stint at freelancing about six moths ago, and have been thinking of writing a similar post at the six-month mark. But to be honest, I wouldn’t have been nearly as genuine or open as you were. At least, not without having read yours, first.

    It’s really reassuring to know that I’m not the only one struggling with this stuff. That’s the biggest thing (for me) about freelancing: feeling alone. Thanks for chipping away at that.

  • I can say, after a decade freelancing (and prior to that, the corporate world) that some of these difficulties don’t go away (you do get better at handling them!). I’ve found that the greatest weapon I have against letting the hard stuff get me down is that I only take projects that I find valuable, that have meaning beyond the job itself. For me (it is, of course, different for everyone) that means working with cultural and human rights organizations and authors. Some projects are better than others, but if the ‘who’ or ‘for what greater reason’ matters to you, it all becomes worth it.

  • Comment by Katrin
    May 2, 2014

    What a wonderful, fantastically written article. I was nodding and thinking ‘Yes! Exactly that!’ at least every other sentence. Thank you (and the wine) for sharing.

  • Hey, great stuff here on what it’s “really like” to be a freelancer. I especially love the part about the real questions you’d love to ask.

    Have you ever checked out It’s all about the business end of freelancing as a designer. Maybe you’ll find some confidence there or just other people to commiserate how damn hard we all work!

  • This sounds exactly like a post I would have written had I been in your exact situation. I figure myself front-end, it’s what I do most days at my job, but I’m actually not all that great at it. In fact, I really lack the jQuery/Javascript skills. Yeah, I can hack something minimal together but not write it myself nor come close to fully understanding how it’s written/read/works. I am very much where you are with how I feel about what I do, what I’d like to do and what I absolutely don’t want to do.

    Ugh, this was refreshing. Thank you for sharing as you are someone I admire.

    Keep on!

  • Comment by susie
    May 26, 2014

    hey! i don’t know if things have changed for you in the past month or so – but what i can tell you is that a lot of what you grapple with are things that freelancers of any years of experience do as well. there are always mysteries behind client door #1, 2 and 3. But, being able to make your decisions independent of a supervisor is key and keeps you from feeling like you did less than your best every time. Plus, I think it’s just really great to work from home and even all hours, even when the pay sucks, just knowing that everything you’re making is yours. Wishing you all the best!

  • Comment by Tim
    June 5, 2014

    This is eerily accurate to the situation that I’m facing as well. Sometimes it just seems pointless to deal with the stress of running every component of a business, with sometimes very little reward when you could easily work a straightforward full time job. I have to remind myself every day why I’m doing it, and justify to myself that I’ll reach my goals. Thank you for being so honest about this. It’s a breath of fresh air to know that so many people struggle with the same things I do. Stay strong!

  • Thanks for writing this Meagan! I’ve recently gone back to freelancing full time after working a full time job for 2 years. Before that I stumbled into freelancing and when things got tough I jumped at the first job opportunity. So here goes another try at freelancing…
    The toughest thing for me is to remember why I made this move in the first place – to work on the kinds of projects I want to work on and have more freedom over the work that I put out. But it is extremely challenging to give yourself that pep talk when you’re low on work and getting desperate. I have to remind myself not to run and look for a full time job that gives me a set salary – that’s a quick fix and I want to learn how to sustain myself and work on projects that excite me. We can be our own worst enemies and the doubts creep in as soon as you face a problem or a lull in work. The challenge is to continue moving along in spite of them.
    Aside from the stresses of dealing with clients, which you’ve mentioned so well in your post, I think the hardest thing is remaining confident in yourself and your abilities and to continue hustling and keep your eye on the ball. I have to remind myself that if I’m having a creative slump, I need to step away from it for a little bit. If I’m having a tough time with a project or a client, well, everyone has tough times and when you’re working for a company you don’t always have control over it, but in freelancing, you have to find ways to make things better and that helps us grow and learn. If all else fails, at least we know not to do that again.
    On the day-to-day front, I’m trying to learn to say “No” and follow my gut. It’s VERY hard to do that when you need cash flow, so my plan is to manage things better and keep a healthy flow of it so I can remember that saying “No” is okay. Sometimes I doubt myself and think I’m working for the client so I should do what they want, but I have to remind myself that I’m the specialist and what I say matters – they didn’t hire a yes (wo)man if they’ve hired me.
    It’s a challenging and risky road but I have to trust that with time and experience I’ll get better at it and at least I’m growing in a way that makes me feel satisfied.
    I don’t think we all have the answers but sharing these stories and what we’ve learned definitely helps. Your post is making me think about sharing my own experiences, with the honesty, like you have. Thanks again!

    One resource I’d highly recommend is Mike Monteiro’s book “Design is a Job”. I read it and almost highlighted all of it. I think it helps to re-read it everytime you have any doubts.

    Good luck and keep writing – I’ll do the same.