A Free Agent Journal

A Free Agent Journal
(Josh Rensch) #12

Way to go @justindirose. I look forward to reading about your adventures in freelancing. It will be exciting to see it through your eyes.

(Justin DiRose) #13

T-Minus 1 Week

This has been a week to remember. My grandfather passed away, so on Friday I hopped in the car to drive 6 hours one way to see him one last time. It was a long day in the car (12 hours and 750 miles total), but it was worth every moment. I’m getting ready to do the same later this week.

I’m in the process of writing a long-form post about it and other happenings in my life that will end up on my blog. The main premise is life is full of departures, and, while they’re not easy, they are the catalyst of new seasons.

Amidst all of this, I haven’t had a lot of headspace to think about going self-employed, funny enough because it’s only 5 days away (technically 3 working days as I’m on funeral leave part of that time).

Periodically, I find myself a little worried about the financial aspect of going out on my own. I catch thoughts like, “am I going to have enough income to support the needs of my family? Do I have enough runway to get through the transition?”

The truth is yes. But now it just looks different. That “different” I’m still wrapping my mind around.

On the marketing side of things, I’ve been working on making some changes to my website (slowly), and I’m finding it fun to have a real home on the web now that’s not just a side project. And now I’m finding little opportunities that I before wouldn’t have noticed, like saying, “Oh, I have an idea for a better way to do this…”

In some ways I wished I would’ve been out on my own sooner, but I know the transition time is perfect.

On another note, I’ve completely redone my desk setup. I’ll create another post for it for you to look at. It’s pretty fun!

(Justin DiRose) #14

Launch Week!!!

This is it. I’m officially done at my old job. After numerous goodbyes and a pizza luncheon, I walked out of my old workplace last week Friday shortly after 1pm. It was a calm ending to an otherwise chaotic week (which I wrote about in my Departures post if you missed it on my site).

My first hours as a free agent were spent packing to go on a trip with the family. And I fully relished the experience, all to the point of not needing to come back on Sunday to work Monday. My work is now wherever I am. That’s a fantastic feeling.

In making the jump, I expected to have a heavy weight put on my shoulders, as if the whole responsibility of providing for my family rested solely on me.

That’s not what happened.

Instead, I feel light, very light. I don’t have a clock staring me down every morning, racing ahead of it as not to be late. I don’t have a million unexpected issues, emails, IMs, or phone calls I’m anticipating throughout the day. I’m not stressed.

I liked my last job, but I’m loving this so far.

It’s not all sunshine and rainbows, though.

There’s still the looming concern of finances ahead. I know I’ll be fine but that worry tries to creep itself in there regularly. Instead of dwelling on it, I reject the thought and remember that I’m free to be as successful as I choose to be.

There’s also finding new patterns of behavior. I’m using some new morning and evening routines that have been helpful, but I’ve thusfar gotten stuck on ending my workday. I have a shutdown routine I sometimes do. At the old job it didn’t matter so much. Now as a developer, my brain needs tons of space to gear down from coding mode to family mode. This will be a work in progress.

Interestingly enough, I’ve hardly used OmniFocus this week. Instead, I am laying out my priorities and schedule on paper for the day and sticking to it. Without all the interruptions as with my old job, I can actually do this now, and it’s freeing. I’ve always worked best with a loose plan, not stringent to the minute but not free-wheelin’ either. What I’m currently doing is a great balance between.

I’m sure the gloss will wear off eventually, and the costs of being a solo entrepreneur will surface at some point. Even at that time, I think I’ll find the benefits of being a free agent more satisfying and liberating than being an office worker again.

I will be launching an email newsletter soon, and when I do, I’ll post a link here so you can follow along with all my future adventures.

(Wilson Ng) #15

Whenever I feel down about things like this, I make sure I have projects that can chip away at these fears. When I don’t know where to start, I just start on any project that will solve the problem/monster-under-the-bed of the moment. I feel so much better when I know I’m actively engaging and working on a problem to quell those fears. I feel worse when my instincts tell me to turn off the lights, curl up in a fetal position, and hide under the blanket.

The less time spent in our task manager gives us more time actually doing the work! Using pen-and-paper to hold today’s priorities and schedule has been my favorite method of working on the day too!

Looking forward to hearing your Indiana Jones adventures. Even Indy has to spend time brushing away dust on some old bones in a cram-packed classroom every once in a while.

1 Like
(Mat) #16

The biggest difference I see is that mind node is visually prettier and Ithoughts is able to give you more flexibility in terms of views. Especially the Gantt chart is nice.
Of course, you could export that mind node file anytime and view it in Omni plan or any other Gantt producer out there, but it’s nice not to have it all in one go.
Setapp made testing the app a breeze😍

(Justin DiRose) #17


Okay, maybe not stress free, but, boy, do I feel a lot less stress. A lot.

I mentioned this a bit last week, and as I’ve thought about it, I wanted to expound upon it a bit more.

The main areas I feel less stress in are all to do with demand — demand on my time, mental resources, and emotional capacity.


This is probably the most obvious one. When I worked my old job, I was locked in 8a-5p every weekday. I could flex a little bit in that timeframe, say, if I wanted to move my lunch break to run an errand, start a little earlier, etc. Even in that flex, the demand was at least 40 hours every week.

Sure, I could’ve worked a few hours on a weekend to make it up leaving early, but I was supervising a group of technicians who needed answers from 8a-5p. I couldn’t effectively do my job after hours unless it involved no human interaction, which wasn’t often.

This demand on my time made me feel stressed, even when I was working from home. When working from home, I didn’t feel like I could go play with my kids or talk with my wife for a few minutes because I was locked into the clock.

Now, as a free agent, I set my own hours. I do some hourly-based contract work, so I still need to hit an hourly mark per week, but as long as I hit that, it doesn’t matter when I work. I like that.

Case in point is yesterday. At 9am, my wife calls me and says we need to run to the clinic because my son got hurt. I ran home, got my wife and kids in the car, and drove off to the clinic. Thankfully, it turns out my son’s injury wasn’t all that bad.

While my wife and son were in the clinic, my daughter was napping in her car seat in the car. So, as any good freelancer would do, I pulled my laptop out (sitting in the driver’s seat, mind you) and continued to do some work while I waited.

While I had flexibility like that at my old job, the responsibility on my time was to someone else, not to myself, which added stress. Now that I’m responsible for my own time, I feel empowered all the more to make sure I’m taking care of everything I need to in a given day, even if that means taking an hour or two away to deal with a family situation and stacking those hours on another day.

Mental Resources

I made mention last week about how my work made me feel “always-on”, with a phone call, IM, or email always coming in the pipe needing to get dealt with in a short order.

Before getting into these effects, I want to take a moment aside here to address the productivity concept of shutting out these distractions to get work done.

You can’t do that when that is your work.

As a maker, sure. You can shut email and IM all day long and process it once. But as a manager of people, your job is to make sure their needs are met in addition to getting your work done.

It makes for a tricky situation. Thankfully, there are limits you can impose on yourself to help weed through the battle, but that’s for another post someday.

I did impose some limits on myself for checking email, answering calls, and responding to IMs. However, since most of my work came through these avenues, staying away from them was not all that easy. If you’ve ever tried to get work done during the day, and you have these inputs coming at you, I think you can probably relate to how draining it can be on you mentally.

I remember multiple instances where I went to OmniFocus, picked a task, started to work on it, and proceeded to get pulled in 5 different directions within 60 seconds. Finally, maybe 5 minutes later, I remembered what I originally set out to do and began again.

That kind of context shifting is exhausting, yet in some capacity, my previous work required it.

Going out on my own has been the most freeing experience in this regard. I only check email when I want to, and send IMs only when I need to. The mental capacity I now have can be fully devoted to creating things, something I had longed to do for years. Now it’s here, and it’s grand.

Emotional Capacity

I’m an introvert, not all that shy, but being around people most definitely drains me. I’m no stranger to remote work, and my last job was the epitome of such — managing employees 100% remotely.

Remote work has its benefits as an introvert; however, it’s amazing in a ~1,5000 employee organization how much you have to interact with people you never see.

If you’ve ever been in leadership in a semi-large organization, you know the number one tool use to get work done: meetings. There were some of my days where meetings dominated my calendar. Since I was a remote worker, that meant phone call after phone call after phone call after phone call.

I remember one fellow manager quipping about how she would have a full schedule of meetings she could hardly think after 2pm.

A day full of meetings is a dreadful ordeal when you have lots of work piling up in your email inbox and IMs throughout the day. Thankfully I didn’t deal with that as much as others, but the regular cadence of meetings did consistently drain me. Combine this with having a couple extroverted family members and the desire to get as much time as I can with them, and you have a recipe for a drained introvert tank most days.

On my own, I get lots of introvert time! At the end of the day, I end up feeling like I’m ready to go spend some quality time with my family, which I highly value and hold as a big rock on my calendar.

Not all of my stress will go away as a free agent. Other stressors will get introduced over time. This early in the game, I’m feeling great, and I can’t believe I’m here doing what I’ve longed to do for so long.

I’m wondering if the glow will wear off at some point still. It hasn’t yet, and I don’t know for sure if it even will. This is a dream realized, and I hope not to forget that!

(Wilson Ng) #18

I do remember being scared and timid when I had to lone wolf it. The first couple of years was more about building thick skin, practicing my craft, and eventually getting comfortable in my role.

Now that you don’t need collaborative features, I’m guessing that you’re going back to OmniFocus? Or are you still mixing it up and switching back to Todoist when you need to collaborate with others? I wonder how much your OF workflow has changed now that there are new features?

Smooth sailing on your journey!

(Justin DiRose) #19

I never really needed collaboration, moreso a Windows client. But yes, I’m back with OmniFocus! I have it on my list to do a deep dive at some point but it’s a huge mess right now while my workflow settles out (and OF3 for Mac is not yet installed).

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(Justin DiRose) #20

I made mention last week that I would be launching an email newsletter. Well, here it is!


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(Michael Herman) #21

I’d love to see your mind map more clearly. I’m currently experimenting with using Bullet Journaling and I’m not sure of the best way to fit Omnifocus into my workflow.

(Justin DiRose) #22

Week 3: Timeyness

In reviewing the last week of my self-employment journey, one item stood out as something I hadn’t been as conscious of prior, but am now at a heightened level: the use of my time.

My professional life started off with hourly roles, then, for the last 5 years I was in salaried positions. The funny thing is, especially with salaried positions, they don’t reward efficiency. You’re not punished if you get the work done in a reasonable timespan; however, if you’re efficient, it doesn’t matter. You don’t get paid more or less; only more work gets added.

Being self-employed, on the other hand, requires efficiency and effective use of time, especially if you’re billing hourly.

While I’ve always desired to be efficient, all the little inefficiency holes became glaring in my free agency. For example, if I take a break to do something unrelated to the project on which I’m working to reset my brain, and I spend a little longer on it than I expected, I feel bad billing that time, so I end up needing to work longer hours to compensate. If I do this a couple of times in a week and I can have a decent chunk of time to catch up on.

Don’t get me wrong. I’m talking 1.5 hours tops here. I definitely don’t have a problem wasting 3 hours on YouTube, but since I’m asking someone else to pay me for the time, I better bill appropriately.

Realizing this caused me to consider carefully how I conduct my day and try to stay as close as I can to a schedule without being too rigid to be able to break away if absolutely needed.

Overall, the last week has been pretty good. I ended up having to work a bunch of hours on Sunday (after a total day off on Saturday) to catch up from last week’s emergency. That was something to get used to being that I’m used to working the weekdays vs. the days of the week my wife isn’t working.

(Justin DiRose) #23

I’ll be sure to write something up!

(Wilson Ng) #24

lol. I’m still going through this every week!

Something called “Bills” pops up every now and then and gives me a swift kick in the seat of my pants to get moving on the important stuff that puts food on the table!

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(Wilson Ng) #25

I’ve always thought about our journey into productivity as a series of experiments. We try something out, fail, tweak something, try again. It’s an iterative process that requires us to not rush into something. Take your time and enjoy the experiment. Don’t be in a hurry to try to cram Bullet Journaling and OmniFocus.

I might suggest trying your hand at Bullet Journaling first and get familiar with that process. Then ease yourself into OmniFocus. Trying to run two experiments at the same time can lead to overwhelm and confusion.

Oh, I’d love to hear back from you about your experiments with Bullet Journaling and OmniFocus! If you could, please post up something when you’re ready.

If you’ve read Justin’s posts or my posts, it’s the journey that makes it interesting. Sometimes we know the general direction but not the direct path. Finding that path is the fun part! It’s not always a straight line but we learn something new every time.

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(Justin DiRose) #26

Week 4: Break Yourself, Not Focus

I can’t believe I’m already in my fourth week of free agency. Honestly, it has flown by :airplane:️. I can say some of the luxury of being an entrepreneur is starting to fade. I’m tired, but that’s largely due to my wife working 2 days a week, I’m working roughly 4 days a week, so that leaves me with one whole day off as I watch my two very young children while my wife works.

I don’t mind the schedule, but combined with some craziness over the last two weeks with family and household stuff (read: a tree crashing into the side of your house at 2am. Don’t worry — everyone’s ok), I’m really tired. That’s why I’m drinking a nice large Americano :coffee: right now while the kids rest (not sleep for one of them anyway — that’s another story).

In the midst of the chaos of life this week, I’ve been thinking about focus, breaks, and free time quite a bit, so I wanted to share what I’ve been thinking.

What I Do to Focus

In my new line of work as a web developer, the ability to get deep, focused work done is essential. Working from home, let alone in the corner of my master bedroom, can pose some challenges to keeping focus from time to time. Thankfully, I’ve worked from home enough the last five years where I’ve maintained a pretty good system. Let me share some key points with you.

  1. Headphones - This is a pretty easy one to accomplish. Get some decent closed-back headphones. Put on your favorite focus music (my classic deep work album is Tycho’s Awake (Deluxe Version). You can use AirPods or other in-hear headphones for this as well, but I find closed-back headphones help drown out noise easier at lower volumes.
  2. Routine - I start every workday with a startup routine. It’s basically me processing my inboxes, writing out my plan for the day on paper (or reviewing it if I wrote it the night before), and easing into the day. I have never done well getting up and off to the races right away, so I try to structure my day around that. It’s important to know yourself in this way.
  3. Discuss boundaries with spouse and family - This is the most important on the list if you have anyone else in the house with you. Set expectations on when and how you can be interrupted. It doesn’t have to be rigid, but if you need to get some focused work done, the last thing you need is your roommate popping in to tell you the latest Candy Crush level he beat. Same thing with family — though it can be harder with kids for them to understand. Communication is key. There’s no science to this except trying stuff and seeing what works.
  4. Differentiated space & time - Having a segregated work area is essential, but one thing that can help with minimizing interruptions is a segregated work time. Set hard limits for yourself on how long you’re going to work, and be done at that time. I’m not the best at this always, but I’ve found it helpful as my family knows that when I’m at the desk during these hours, I’m working.

I think over time, I’ve gotten a lot of the interruption kinks worked out. Honestly, the last week has been filled with a lot of long, long deep work sessions. I’ll start work at 8am, and keep cranking on the project until 1:30pm, sometimes without even getting up. I know that’s not super healthy for my body, but I get so into the work I’m doing that I forget what time it is. I’m glad I have work that’s like that, but I need to get better about managing it well.

Taking Breaks

Part of the reason I’ve been so tired the last couple of weeks is I haven’t done a good job of taking breaks. I’ve gotten off my thinking walk habit, and I haven’t been writing during the day much either as I’ve liked. The main problem has been that I’ve been working on a big project. There’s a lot to learn, so I get sucked into doing it until I figure it out. Pretty soon it’s way later than I wanted it to be, and I don’t end up doing what I wanted to do. It’s a bummer, but I think that will lighten up once I finish this project.

Yet the fact still stands that I need to take breaks. I need to add a little margin in my work life. I don’t quite yet know how to approach this one better without feeling pressured to choose between doing work and spending time with my family. There is a balance, but I have yet to find it.


Speaking of breaks and doing other things, one thing I had hoped I’d have more time for as a free agent is hobbies and side projects. In my current state, that has barely been happening. I’ve been writing for the Guild, my blog, and my newsletter, but I also have other side projects I’d like to spend a little time on here or there. One of those is making music. Unfortunately, recording and making music can take longer blocks of time to allow creativity to flow more freely.

I’ve been finding myself feeling sad I haven’t had the chance to do any of this stuff yet. I also realize I’m only in my fourth week of being a free agent. I have a lot of road ahead of me, and I don’t need to do it all right now. That’s the temptation though — jump head first into everything all at once and not be good at the one thing I’m doing right now — being a web developer.

For those of you who are free agents (or want to be), how are you doing? Please feel free to respond in this thread or start a new topic so we can discuss!

(Ed M) #27

I have been an independent contractor (i.e., free agent) for 14 years. The one thought of my own experience I had while reading @justindirose’s report of his week 4 is that for independent gig workers like us there is never any time off. The billable work week might be 30 or 40 hours, but it is spread across all days and frequently all times of the day. In my work it is essential to be current with the flow of client email, to respond to texts asking questions or opinions timely, and to produce whatever deliverables I have been directed to do promptly and completely.

So, if an email comes in at 4 PM asking for a deck to brief an executive on an issue in a 1 PM meeting the next day, then I have to be flexible and get the work done that evening so my client has it first thing in the morning to review and ask for changes.

This always-on-call work pattern is no different than when I was a senior manager in the corporate mold – but the upside of being in a free agent gig is I can choose where I am when the call or email comes in with an assignment, or a meeting invitation, etc. I don’t have to sit in an office anymore, haven’t for over a decade. I can write my reports while watching Better Call Saul or head to the small private “writers room” where I rent space when I need to be away from interruptions. I can be anywhere in the world. Great gig if you can get it.

I think a key success factor in free agency is learning how to quickly turn on work mode, focus, finish the task, then click off. That makes the always-on-call aspect a lot easier to deal with in the work/life balance.

(Justin DiRose) #28

Week 5: Scheduling Conflicts

Internal conflict ended up being the banner theme of this week’s venture in self-employment.

Family needs have been increasing, which has put work hours and such into contention lately and demands something different.

Short term, I haven’t come to a solution yet, but I have a few on the table I’m evaluating.

While you would think it would be easy to make changes, I end up feeling conflicted with priorities. I want to be there for my family to help. I want to have some time off. I want to have time to work on side projects. I want to continue working as a free agent.

With only 184 hours in a week, I have to make tradeoffs and sacrifices to make this work. I don’t want to sacrifice time with my family, one on one time with my wife, going to church, and the like. Yet I feel right now no matter the direction I go, something will lose, but thankfully only for a time.

The other major item on my mind this week is taxes. Here in the United States, the self-employed need to pay quarterly estimated taxes. My first round of this is coming up this month. I sent my numbers to my accountant yesterday, and was okay with the result, but still a little mortified at the percentage of my revenue I pay to the government as a self-employed worker. I’m taking steps my accountant recommended to decrease my tax burden, which is good, but dang!

Ultimately, this is the new reality of being a business owner. The beauty of it is I’m the owner. I can solve the problems I have. I would’t be able to figure out a different schedule in an 8-5 jobby job, or work with my accountant to deduct additional items for my business I didn’t think of. It’s on my shoulders now. Frankly, that’s a freeing — and frightening — thought.

(Justin DiRose) #29

Yes, for some kinds of work this is extremely true.

Thankfully, I’m contracting for an agency where my responsibility is to get the project work done, so there isn’t a lot of “always on” time. However, regardless of your work, the business is always your responsibility as the owner, so it can definitely weigh on you. I think @joebuhlig mentioned on the recent Whims at Work episode that he has ideas for his business usually 15 minutes before going to sleep. You can’t get away from something that’s yours. Though the prospect can be scary at times, I’m really okay with that reality.

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(Justin DiRose) #30

Week 6 - The Challenges of Remote Work

I wanted to check in with you all this week on my scheduling dilemma. I decided the best approach is to work more days in the week, but fewer hours. This week has been test week for it, and I’d say the experiment so far is successful. I feel a lot less pressured in other areas of my life, partly because I have time to do other things I like, such as having lunch with a friend.

That brings up another topic I’ve run into a lot lately. Folks who work remotely or are solo business owners working out of their homes in the digital economy often tend to deal with loneliness, depression, or anxiety.

Doist recently had an article focusing on just this — the dark side of remote work. Working from home or anywhere in the world is often touted as this dream job situation, but unless you structure it carefully, it’s often not what it’s cracked up to be.


A few remote workers/business owners I’ve communicated with recently have told me they feel something of this sort. I’ve gotten to that point at times myself, but I have found being intentional with time in relationships meets that need for connection.

The culture of remote work is amazing, but at the same time, we’re wired for community. No amount of conference calls, chat rooms, or social media replies will ever take the place of driving to a coffee shop to chat face to face with a friend who truly knows you. We’re wired for community, and the fullest expression of this is in-person interaction.

To combat this challenge inherent to remote work, I’m doing three things:

  1. Setting boundaries on my work time
  2. Intentionally getting out of the house weekly
  3. Scheduling time with friends, both for myself and my family

Community and connection is always an intentional endeavor. It takes a lot of effort to maintain relationships, especially even more so in the age of remote work and internet-based jobs, but the investment is absolutely worth it.

If you’re a remote worker or free agent, how have you navigated these challenges to stay connected and maintain relationships? I’d love to hear from you.

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(Justin DiRose) #31

Week 7 - Acquisition

You may have heard already that I’m the new owner of the Guild! What a new and exciting time. I think it’s wild I’m taking this on only 7 weeks into my free agent experience, but I’m grateful and anticipatory for the opportunity.


When Joe approached me about the opportunity, I immediately went into dream mode. About a thousand ideas came for the Guild all at once. It was amazing and overwhelming all at the same time. But once that settled, the fear set in. Questions began to fill my mind, such as —

  • Do I have enough time?
  • What if it doesn’t work out?
  • Does this even make sense right now being so new to self-employment?

My wife and I started discussing the opportunity immediately after Joe asked me. We contacted mentors and advisors for their advice.

From there, I spent some serious time thinking about the questions I listed. Most of them were just fear-based and had no scope in reality. Additionally, I’m still getting used to the mindset of being a business owner who can make strategic investments, so I think a little insecurity was coming through there.

Fear and insecurity are the two largest items that can hinder a person’s growth. Letting fear overtake me has actually hindered me in the past. I’m not interested in going down that road anymore. When I’m afraid, I can’t dream of the possibilities of the future. When I can’t dream, it’s hard to go in any certain direction.

The funny thing about fear is you can feel it, sometimes even strongly, but not let it make decisions for you. Fear-guided choices are exactly what takes the train off the rails.

How do you combat fear, then?

  1. Recognize it. - The key to navigating any kind of negative emotion is to first recognize it. This is half the battle.
  2. Disconnect from it. - Try to get above the feeling to see the situation for what it really is.
  3. Talk to someone trusted about it. - Especially if you are having trouble getting above it, talk to advisors and mentors about the decision/opportunity/etc. causing fear. Often they will have helpful insights you might not be able to see.
  4. Make a decision apart from it. - Whatever you do, don’t let fear make a decision for you. Make a wise, informed choice (I.e. don’t just quit your job because you want to when you don’t have anything else bringing in income).

These items obviously won’t apply in every situation, but they can be a helpful starting place to evaluate overcoming something you’re afraid of.

I’m really excited to see what we can do with the Guild in the coming months. There’s so much potential here, and I’m looking forward to tapping into it!

As a meta update on this journal, I will write one more weekly post next week. Afterward, I plan to continue updating on a monthly-ish basis.

Thanks for sharing this journey with me!