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#DearID Episode 49: Season 4 Opener

In: Dear ID Showelearning

In this episode, we start the long-awaited Season 4. The theme this season is freelancing as an instructional designer and we start by talking about the highs and lows of my freelance journey.

Be sure to check out a transcript of the episode below the player. And the shownotes are here:

Hey everybody and welcome back to Dear Instructional Designer, the show about the instructional design journey. I’m your host, Kristin Anthony.

It has been a long time coming but it’s finally here. It is season 4 of Dear ID. Ah, it feels good to be back to be talking with you all and we have a great season planned for you. This season we’re all taking a jump off the deep end and talking about journeys into freelancing. This season’s theme just came to me from a bunch of different directions actually. As always, I keep an eye out on the instructional design subreddit to see what sorts of questions people are asking there and how to become a freelancer has been a hot topic recently. I also got an email from someone who will be a guest this season asking about the show and wanting to talk specifically to freelancers, and I thought that this would be a really great theme for us to explore together. You see quite a few independent IDs out there but we don’t always or often see the process behind how they’ve been able to start their business and keep it going and find clients and all of those particulars that anyone wanting to go out on their own really wants to know. So I’ve got several guests lined up this season who are in different stages of the freelancing path who will help us to answer those and I’m also going to speak about some of these pressing issues from my own perspective, now a little over a year in to my own freelancing journey. And that’s all going to start with this episode, where I am going tell you a little about how I fell into freelancing.

So I want to start by saying that I really had no intention or plan of ever being a freelancer. That was not anything I had ever thought seriously about. But as my portfolio grew and I continued with the blog and the podcast, I started receiving emails from people wanting to know if they could hire me and I took on a few side gigs to make some extra cash. So even before I took my job at the software company, I had been doing a little bit of freelance work on and off, but I wasn’t sure that I liked it. I was getting the kinds of gigs, as you might imagine that were on the order of, “I need an elearning developer to do stuff (mostly click and reveal) with Storyline.” And one the one hand, it was fairly easy because I had my own copy of Storyline and my own computer and it was stuff I could do. On the other hand, it was difficult and time consuming, partly because I was coming home from work and doing more work, which majorly cut into my time to concentrate on my own side projects and partly because it felt really tedious. I was having to do all of this visual design, deciding on a color palette and typography and interaction design, but I think the thing that kept me most from enjoying it was that it wasn’t really the kind of work I wanted to be doing. I had no say in the instructional design part of it, which, for all that I’ve said on this show that I love development work (and I do) I’ve become the kind of person who needs to be able to ask a lot of questions about design function and I think that trend is continuing in myself as I work on my web development skills. Why is this here? What is the function of that? What are we trying to get across with this? And I think as a result of not being clear on that up front, I was allowing myself to say yes to clients who weren’t looking for that kind of input and it made the entire process a slog for me. I really wasn’t really enjoying myself much.

But what I was enjoying through parallel to this whole freelancing process was those side projects, particularly learning more and more about programming and experimenting with xAPI. Throughout the year I worked with the software company, I had been taking more self-paced learning, been building side projects, and had joined my first xAPI cohort so I was really in tune with the idea that I could be building cool stuff and trying to solve cool problems. And I realized that when I talked about loving development work, it wasn’t the type of “here’s some content, build a course” development, it was more about being able to solve really interesting challenges through prototyping and building and shipping products. It was the entire process of solving a problem through development that fascinated me. I’d been looking around for coding bootcamps that I could do part time and, as I advocate here on the show, I’d also been telling everybody about what I wanted to be doing and what skills I wanted to be building. But things weren’t exactly working out.

So one day, I was working from home when I got a call from a team I had previously worked with at the university I left and the guy told me that they were trying to create a catalog of courses for themselves and that, along with that they wanted to build a platform to market and sell those courses and that they wanted me to be involved. And the guy I was talking to knew that I was really interested in getting better at programming and so he understood that this would be an opportunity for me to build a real-world application, this would be a major opportunity for me to learn and produce something that would be used by hundreds of real customers. And as with most things that terrify me, I knew that this was one of those big opportunities that don’t come by very often. So I was really excited by this. This felt like a different kind of freelancing opportunity; one where I would actually grow in the process.

But of course, I had a full time job and I’d only been there a year. So, not wanting to just jump ship, I tried to have a talk with my supervisors about going down to part time, so that I could pursue this other opportunity to build my skills. Unfortunately, that did not go over too well. My employer did offer to involve me with a project that would have been trying to tweak and improve their current learning portal, but to me it just wasn’t the same opportunity for growth. So they gave me an ultimatum and I decided that I was okay with leaving to do this really scary, possibly very stupid thing.

After a couple of week of wrap up (I tried to give them 4 weeks notice, but they decided that they didn’t need me after about 2 weeks), I fired off an email to all of my colleagues thanking them for their work and I was officially a freelancer. And then reality set in.

Here’s where I insert a warning to NOT do what I did. While, as I said, I’d done a bit of freelancing on the side and as I prepared to go full time freelancer I looked up several articles and resources on things like pricing, I don’t think I had a good grasp of all the things a full time freelancer needs to work into their pricing structure. It’s not enough to simply take your current salary and try to calculate an hourly rate based on that. You need to think a lot bigger because you’re paying all of your own taxes and all of your own healthcare (which have been my two biggest expenses) along with of course your own software tools, and all of the other things that you normally pay for . And I’ll admit I was afraid of pricing myself out of opportunity because I still didn’t feel experienced enough to be charging big bucks. But the bottom line is that I ended up working like a dog, 70 and 80 hour weeks, the podcast suffered, my blogging habit suffered, my health suffered, I was having to find new clients and work some more and I still wasn’t really bringing enough home.

The work itself was a challenge, too. I was working in parallel to develop a ton of courses with SMEs who had never developed online courses before and many of whom had never even taken an online course. There were a ton of process problems that cropped up, too. As I tried to create a repeatable process we had a lot of non-compliance. People didn’t want to use the tools or they didn’t communicate in a timely manner or they complained that I hadn’t given them resources. Yes, I even dealt with adult-level temper tantrums! And with some of my other clients, I didn’t even implement process, as I tried to rely on their internal systems. This led to even more frustration. I was also helping to develop this course platform which brought its own frustrations from difficult programming challenges to feeling like the team was making bad decisions and not feeling heard. There were so many times, when I wanted to just fire everybody, including myself.

To sum this all up for you, friends, my initial 9 or so months of freelancing was absolutely hellish. And I have grown SO much by making it to the other side of that. I think that the three biggest things I’ve learned by crash-freelancing, if you will, that I want to share with you have been how to be more straightforward, how to talk about process, and how to set boundaries.

First let’s talk about being more straightforward. Some time back I read Mike Monteiro’s Design is a Job and one of the lessons that stuck with me is when he talked about being that designer that says no and has an opinion and pushes back, even if that doesn’t make you the most likeable person up front. We’ve talked about this on the show before, I know that this can be really tough because on some level, we are there to make the client happy, but I think that at a higher level, we’re there to make the client happy by getting them the results that they want and to do that, we have to rely on our expertise and sometimes that means saying, “I’m against us doing that and here’s why…” I think that going through everything that I’ve gone through, and I will say being able to go through it with this particular set of people who I really do feel I can be honest with, has helped me to be much more articulate and straightforward with feedback. I’m not shy anymore about saying why I disagree with a decision. Even if I don’t win out, I say something. And one of my mentors helped me to understand it this way: he says that one of the benefits and the responsibilities of being an outsider, which you are as a freelancer is to be able to talk candidly about the issues. While people who are in the organization probably see the same issues, they’re reticent about saying anything because these are the people that they work with day in and day out. In your case, while you want to build relationships, you can afford in some sense to build those relationships on honesty and mutual respect. You can talk about what you’re seeing, and of course, offer up some solutions to tackling the problems. Don’t be a jerk, you know that, but do be honest. I really feel like this is one area I’ve transformed in. I let people know up front how I work and why and then I proceed to work that way.

On a related note, I have learned so much about the importance of good, transparent, repeatable processes. When I first started out as an ID, you all have heard this story, I was in an organization that had its own process and I knew even then that this was a great way to prop me up because I didn’t know much, but at the same time I was a bit fast and loose with it. Sometimes it felt restrictive and even silly. Now, there is such a thing as bad process, but having lived through my initial freelancing experiences, I am now a huge believer in process. It is the number one thing that can stand in the way of my velocity, my ability to work efficiently and effectively. As time wore on with that first client of mine, I learned about tools, for example using Trello to track work, and ways of working, for example commiting to some measurable chunk of work in a given time period, working in sprints, that has pervaded the way I work even on personal projects. Again, when I was first introduced to these methods, they seemed overly cumbersome and we have done a lot of tweaking but the core tenants have been huge in transforming the way I work and in doing so, they transform the way I communicate with clients and the way they can see the value I bring. By using tools like Trello to track work, I place value on transparency. If I’ve pinged a SME a couple of times and haven’t gotten a response back, that Trello card goes into a blocked column and everyone can see exactly why. As I’m working on some issues, the cards are moving towards the right in the columns on the board so people can see exactly what I’m working on right now and the list of things I’ve completed and all of the mini tasks that had to get done to get the larger task completed. It transforms, I think, the sense of ownership and accountability because everyone can see what you are doing and what you aren’t doing.

I also find that commiting to a certain amount of work in a sprint of a week or two weeks allows you to identify process problems, quickly. If we get together and decide that we’re going to do this amount of work by X date and it doesn’t get done, it may be time to get together and talk about how realistic the client’s timeline is. And the board and the work is the evidence. The way I’ve learned to do sprints also inherently involves review. So once I’ve moved a card into a Ready for Review column on Trello then it’s time for someone from the owning organization to deploy someone to verify that the tasks listed are complete. If review happens, then the organization identifies problems early on and we work efficiently. If review doesn’t happen and they identify problems later, that’s another opportunity to discuss the importance of review and how NOT performing that affects their product and their timeline and again, in this instance, the Trello board is the evidence of what occured. So this is the way of work that I have learned to bring with me everywhere. And I stick to it and I hold clients to it and whether it’s going well or it’s bumpy I have this body of transparent communication to talk from.

Last, I’ve learned to set boundaries. I love to work. I find work interesting. But there was this huge chunk of time coming off of months of those 70 and 80 hour weeks where I didn’t want to work at all. Cue the “I don’t really wanna do the work today” song. I couldn’t focus and I didn’t want to. I didn’t even want to do any side projects. And that was a huge red flag to me. I had suddenly lost all interest. I realized that I needed to stop. I was burnt out. I needed to make time for rejuvenation, things like reading and walking my dog, and just going outside, and yes, working on side projects because that’s when I get to do fun stuff. And, again, I want to recognize that I’ve been super fortunate because I’ve been able to let some clients fade away but with my major clients, I have the kind of healthy relationship with them that lets me be honest and as contract renewal came up, I talked candidly about the problems I’d been having and I set boundaries, like not expecting weekend work and a limited number of hours per week. I’ve learned how to have those conversations and how to work in mini habits (in fact I recently finished the book Mini Habits) around working back in things like reading every day and doing a bit of exercise every hour. And I’m feeling so much better.

That has been my journey thus far as a freelance learning experience designer. It’s been rough, but I’ve grown enormously. I sincerely hope that hearing that allows you to make your own journey a little bit easier, or if you’re already travelling down a rocky road, to let you know that you’re in good company. I screwed up too, but I’m back on track and feeling good about the future. It’s not too late to recover.

That’s it for this episode. Hey if you’ve got questions about the show, questions about my freelancing journey, get at me: I’m @anthkris on Twitter, or you can shoot me an email at kristin AT

And don’t forget to leave a review on iTunes! Your review helps other people find the show and lets me know how I’m doing. I would really, really appreciate it.

Thanks so much for listening and I will see you back here next time. Take care!