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Keenan Payne
Keenan Payne

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Goodbye Asana, hello freelancing

It's seven, almost eight months past due, but there's no better time than the present to share some exciting news about my life. I have left Asana, and I'm now working full-time as a freelance web developer! I am a gun for hire, taking my decade of web development experience and applying it to new projects and clients that need someone with my expertise.

Because so much has changed in my life during the past year, I have done a decent amount of reflection, which I think would be useful to share with others. This post will just be a little overview of where I've been, where I'm at, and where I'm going. It will serve more as a personal reflection, but might provide some insight that could be applicable for others.

From Montana to San Francisco

Before joining Asana as their second web developer, I worked as a freelance web developer for several years in my home state of Montana. I started my career working part-time throughout high school and college, and upon graduating from college, I pursued freelancing full-time for two years. As I started looking to expand my horizons as a professional web developer, I found the options available to me in Montana somewhat limited. Working remotely for a company was a possibility, but even in early 2014, there were much fewer opportunities available to those seeking to full-time remote work (fortunately, remote work is much more pervasive now 1).

Coupled with my desire to leave Montana to try living somewhere new, I embarked on a job hunt in employment-rich cities such as New York, Seattle, San Francisco, and even Amsterdam.
After hundreds of emails and applications (many of which were for jobs that I had no idea I was unqualified for 2) I ended up focusing on San Francisco, due to the large technology scene and plentiful job opportunities. Applying to Asana occurred to me by happenstance, as I was brainstorming companies to look into one afternoon. I remembered using Asana with a client of mine (shout-out to Glenn and Jamie) who used the product to organize the work that we were doing together. I looked at the job listings on Asana and voilà, a listing with "web developer" appeared. After countless rejections, I had gotten much better at matching job listings with my skillset, and the listing for Asana seemed like the perfect match. Well, needless to say, that it was as I ended up working at Asana for almost five years.

Overall, I had a wonderful experience working at Asana. I was fortunate to work at one of the prosperous startups in the city. This led to a lot of change during my five years working there. As a reflection on what changed from when I started to when I left, I wrote some highlights that come to mind:

  • I was only the second web developer at Asana, alongside my co-worker Sarah. By the time I had left, we had a team of 9.
  • In 2014 the company was only 70–80 employees, and when I left in late 2019, the company was upwards of 600 employees.
  • I learned a lot while at Asana. Not only about web development, but coming from a purely freelancing background, I had a lot to learn about how to work within a larger organization. This deserves a post unto itself, but a not-so-shortlist includes:
    • Collaborating with teammates
    • Communicating with stakeholders
    • Costing my work
    • Understanding how to make trade-offs
    • Framing my work within the broader context of an organization
    • Handling interpersonal workplace relationships

Looking back, I am pleased with the time that I spent at Asana. There are things that I think could have gone better, but such is the case with most areas of our lives. I met a lot of great people, built a lot of great things, and learned a lot of great skills. That's not a bad takeaway from spending five years working somewhere.

My Asana office setup

My Asana office setup. Why is there a bunch of fake grass on my desk? That was a prank, and I kept it on there for almost two years.

Reflecting on areas of improvement

It may seem difficult from the outside looking in to understand why somebody would leave a high paying tech job with great benefits and security for self-employment, which offers no benefits, precarious security, and is sometimes high paying. Leaving Asana is not a decision I took lightly. I spent a lot of time reflecting on my needs and desires to understand which direction I wanted to take my life. After doing that, I decided that moving back into self-employment lined up most with my goals.

I thought it might be interesting to outline some of the biggest drivers that ultimately led me to move from Asana to freelancing.

Working Hours

I dislike having a prescribed structure thrust upon me by others. I don't necessarily know why, but it's something that I've been aware of for a long time. As a child, this manifested in disdain for attending things like school, football practice, or any other obligation for which I had little personal enthusiasm. As an adult, this has largely manifested in "working hours." That is, the hours under which humans are normally expected to work, which is generally viewed as 9am–5pm(ish). Fortunately for me, Asana was quite flexible in this regard. I could generally show up anytime between 9–11am, and no one would care (however, the implicit expectation, as set by everyone else showing up around 9am, did make my lackadaisical 11am start time feel a bit odd.) Even with this flexibility, I was still largely fitting my life into a general framework that I had very little control over. Ultimately, I ended up not liking the expectation to be somewhere at a specific time, even though admittedly, that rigidity was less rigid than what others generally experience day-to-day.

As a freelancer, I have the final say over what my schedule is. I get to take a look at the work that I need to do on a day-by-day basis and determine how much time is required to get that work done. I then get to fit this work into my day in a way that is more symbiotic with my other obligations and desires. If I feel more inclined to read and write in the morning or afternoon, I can do so, and give myself time to do client work afterward. This is the opposite of what the standard working paradigm is, and it works very well for me.


Not only did I have to be at a place at a certain time every single day, but in order to get to that place I had to commute. You know, I had a commute in Montana to and from my office in Missoula. That commute involved getting in my car, driving 1 mile east for 5 minutes, parking my car, and getting out of my car to walk up three flights of stairs to reach an office. This was a tolerable commute. Hell, I would have tolerated an extra 10 minutes on top of that so long as the weather wasn't terrible.

What did my commute look like in San Francisco? I'm glad you asked. I would hop on one bus that would show up whenever it felt like down the street from my house and take that to Van Ness street. This is already a rude awakening since Van Ness is where the downtown San Francisco techno-dystopian hellscape begins. I would then wait for another bus that shows up whenever it felt like and ride that until I got close to my office, where I would then walk the remaining distance. This whole process took anywhere between 35–60 minutes on average, depending on the inclination of the San Francisco Municipal Transportation Agency. I will note that this was when I lived 2.5 miles away from Asana. I decided to move further west in the city because my rent had increased, and I wanted to save money and get further away from the busyness of the city. This additional two miles added another 15 minutes on average to my commute time and put me on a bus that was, on average, packed with even more people trying to make their way downtown.

Needless to say, between having to be somewhere at a particular time and having my mechanism to get there be a (sometimes literal) shitstorm, the morning was not always my favorite time to be a human being. Enjoying my cup of coffee without somebody blasting a boombox and rolling a cigarette in the back of a bus is ideal for me.


Oh boy, let's talk about meetings. Over the course of my five years at Asana, the number of weekly meetings that I attended, and the duration of those meetings, increased year-over-year. In the beginning, there was a weekly team sync, as well as a one-on-one meeting with my manager. These were my standing meetings, and any other meetings, which occurred pretty infrequently, were to discuss project related or company-wide matters. I was very happy with the ratio of work to meetings in my first few years at Asana.

As the company grew larger and, specifically, the web development team grew larger, so too did the amount and duration of our meetings. In lieu of finding other processes by which to mitigate our meeting load (cough, the product we were building), the fallback had become more frequent and even longer meetings. If you've been following along, this falls under "being somewhere specific at a certain time." This is something that I do not enjoy, but its effect is even more pernicious, given the interruption that meetings cause during the day. Meetings force context switching, which, if you're unfamiliar, is horribly unproductive.

As a freelancer, I have, on average, 1–2 meetings every week, with no meeting lasting longer than one hour. Many weeks, I will only communicate asynchronously with clients and collaborators via Slack or Asana without the need for a proper meeting. Do you want to know something? All of the work that I need to do is still getting done, decisions are still being made, and everyone is up-to-date on project progress. In fact, and I have no hard numbers to back this up, but freelancing feels way more productive than working in-house 3. Fewer meetings play a large part in that, but they are only part of a higher order category under which productivity is achieved, which is minimizing context switching—more on that in one line break.

Context switching

Context switching is the act of moving from one context—that is, the conditions under which something occurs—to another context. This is normal and something that happens constantly throughout our daily lives. However, to achieve maximum productivity doing something, you need to be focused on that something. Focusing requires both deliberate effort and minimal distractions. I have the former in spades, but I had the latter in undesirable quantities while working in an office.

This isn't anything specific to Asana, but I believe it's mostly a result of the office environment in general. Asana is full of a lot of great people that I enjoyed being around and conversing with, and if you know me, you know that I love conversing. There is both good and bad to this. The good is that I have the privilege of being around a bunch of humans that I enjoy on a daily basis. The bad is that being around those humans created an amount of distraction that detracted from my day-to-day productivity. Whether it was so-called "water cooler talk," answering questions and helping co-workers, attending meetings, or any of the other number of things that can happen as a result of working with hundreds of other people, I was distracted. This had a negative impact on my ability to focus, which had a negative impact on my ability to do my job effectively.

I could take my laptop and work in more remote areas of the office to avoid other people. However, this came at the cost of sacrificing comfort for focus. I like working at my desk with my split keyboard, huge monitor, and a comfortable chair. I am generally more productive working at my desk than anywhere else, but I am also more productive when I'm not being distracted. Unfortunately, working in an office forced me to choose between one or the other, which ultimately led to dissatisfaction with my work environment.

Since I started freelancing, I have primarily been working from home in a desk setup that I configured after leaving Asana (and realizing that my Ikea desk and chair were going to be the death of my back if I didn't upgrade). Now, I have the best of both worlds: I have a desk configuration that is perfectly situated for how I enjoy working, and I have an environment that is conducive to focusing. The only thing I'm missing is face-to-face contact with the people that I enjoyed seeing every day at Asana. I've mitigated this feeling by being proactive in scheduling time to see my closest friends regularly so that I am not lacking in human contact.

My home office setup

My current home office setup. I will share a post about how I decided on my equipment in the future.

Professional agency

Lastly, and perhaps most importantly, was the distinct lack of agency that I felt over the work that I was doing at Asana. I take an immense amount of pride in the work that I do, and I always strive to do the best work that I can given the circumstances. The problem, however, was the circumstances under which I was continually doing work at Asana. As a fast growing startup, everyone is expected to move quickly to help keep the company growing, so that we can continue meeting our goals, so that we can eventually capture the market, so that we can be a sustainable company… so on and so forth.

This is all fine and good, but it came with one problem: we were usually in a state of reactivity instead of proactivity. "How quickly can we build this landing page for a new product" was my life for years at Asana, instead of "how can we design and implement a system that facilitates building landing pages quickly." Instead of reflecting on how we could make improvements to allow for better work in the future, we consistently looked towards the next project that the marketing or sales team needed to meet their goals. This led to building on top of systems that were not designed for the size and scale of work that we were doing, which led to lower quality code, which led to sub-par design implementations, which led to personal dissatisfaction. Additionally, I was usually at the tail-end of a waterfall planning process that usually happened with little or no input from me. As a result, project deadlines would be determined by the time that it was my turn for development, which offered little room for me to organize the work in an ideal way 4.

As a freelancer, a large part of my job is planning and organizing how the work should be done for a project, alongside doing the work. I learned after leaving Asana that I need to create the circumstances under which I create high-quality work, not expect those circumstances to arise from external forces. As a result, I am growing comfortable telling clients that I will be organizing and orchestrating the entire development-side of a project while allowing other stakeholders to organize and orchestrate the areas where they are responsible. This enables me to build web projects that I am more proud of, set reasonable deadlines for work that needs to be done, and build confidence in my clients that I can be trusted to run a web project from start to finish. I am the expert, after all, and this is what people are paying me to do.

Side note

I will note, perhaps unnecessarily, that I am not trying to rag on Asana in any way. The issues that I experienced during my time working there are not uncommon to others who work in an office setting, specifically one that is in a metropolitan area. Even still, in order to create positive change for myself, I need to clearly understand what areas needed changing. My needs and desires might be different than yours, and that's okay. We all have things that we prioritize, and the trade-offs and decisions that we make are going to be a result of that prioritization.

Upward and onward

This was a pretty long-winded post, but there was (and still is) a lot for me to unpack. I also realize that there are more things that I touched on that might be suitable for their own more comprehensive post in the future. Even still, I appreciate you sticking with me throughout all of this; including those of you reading this blog post who don't know me at all, and those of you reading this who do know me and have given me unconditional support throughout all of these years. I appreciate each and every one of you.

As for me, well, I'm now a freelancing web developer once again (well, I have been for almost eight months, but I already went over that). If you are interested in hiring me for a web project, you should get in touch and we can talk more about it. I'm a systems focused front-end developer, which I enjoy working on projects where I can help architect and implement solutions that solve problems, big and small, in an intelligent and scalable way.

If you are reading this and find what I have to say compelling or interesting, I encourage you to sign up for my newsletter. Writing is something that I have wanted to do more regularly for years, but I have not made the time to do it until recently. I plan on writing about my experience as a freelancer, which will include sharing my thoughts and ideas, which you might be able to use for your own career. I will also be occasionally sharing web development tutorials, tips, and musings if that is up your alley.

And of course, if you feel so inclined, leave a comment down below and tell me what your thoughts are. Have you had similar experiences working in an office environment, or is the office environment more conducive to productive working for you? Either way, I would love to hear your thoughts and opinions.

  1. Of course, I expected the transition to remote-friendly work to grow steadily over time, but the unfortunate spread of Covid-19 seems to have kicked a foot into the back of companies' asses who were resistant to setting up an infrastructure that allowed for remote-friendly work. 

  2. Growing up with a completely informal education as a web developer ended up creating some confusion when I tried taking the skills that I had and match them to job listings I found online. I had no idea what I was; was I a web developer, web designer, front-end developer, software engineer, blah blah blah. Anyone who has applied for a technology job before probably knows how horrible job listings are. That, combined with my lack of understanding about what exactly I was as a professional, led me to a bunch of awkward phone calls where both parties fully understood that I had no idea what I was talking about for a job to which I had applied. Oops.  

  3. I may not have hard numbers to back it up, but the number of projects that I have been able to complete during my first six months freelancing dwarfs what I was doing at Asana. Sure, this is anecdotal and there are plenty of caveats I could make, but I'm listening to my gut on this one: I'm much more productive right now than I ever have been. 

  4. I will note that the process for organizing and executing web projects got much better during the last year that I worked at Asana. After years of being at the tail-end of waterfall planning, I was finally having more of a say in the planning process, which allowed for more flexible deadlines and better project planning. However, we still acted as a mostly reactive team, and rarely created time for ourselves to improve our processes and infrastructure.  

Top comments (2)

mlimonczenko profile image

Cool post, Keenan. I definitely think that COVID is changing the game. As someone who has done both freelance and full-time web development, there are huge benefits and tradeoffs to both. Biggest lesson for me is knowing my worth and budgeting realistically.

I wish you luck on your freelance journey!

keenanpayne profile image
Keenan Payne

Hey Miranda, thank you so much for the kind words! I completely agree with your point about working full-time and freelance — there are tradeoffs for both, and deciding on one path vs the other will depend on the person and the circumstances.