Welcome to episode 233 of the Nerd Journey Podcast [@NerdJourney]! We’re John White (@vJourneyman) and Nick Korte (@NetworkNerd_) – two technology professionals with backgrounds in IT Operations and Sales Engineering on a mission to help others accelerate career progression and increase job satisfaction by bringing listeners the advice we wish we’d been given earlier in our careers. In today’s episode we share part 1 of an discussion with Josh Duffney where we check in on his progress writing a nontechnical book over an 18-month period, how his writing processes changed over time, energy management, and focus. We’ll also discuss how Josh ended up getting lost in his career during this period and how he recognized he was there.

Original Recording Date: 06-19-2023

Topics – When We Last Spoke to Josh, Writing Processes and Shelving a Manuscript, Energy Management and Long-Term Projects, Routines and Habits, Lost in Thrashing and the Purposeful Distraction, Persevere or Pivot

4:19 – When We Last Spoke to Josh

• Josh Duffney has returned to share how he’s progressed since we last spoke to him. For previous episodes with Josh as guest, check out (in chronological order):
  • Episode 123 – Just Add Value with Josh Duffney (1/2)
  • Episode 124 – Focus, Create, and Iterate with Josh Duffney (2/2)
  • Episode 156 – Better Notes, Better You with Josh Duffney (1/2)
  • Episode 157 – Take Note of Your Time with Josh Duffney (2/2)
  • Don’t forget to check out previous books Josh has written on technical topics:
    • Become Ansible
    • How to Take Smart Notes in Obsidian
  • Today’s discussions will use this Twitter thread as a backdrop.
• When we last left Josh, he was in the process of writing a book.
  • Josh says it was going well until he got really close to finishing, but he put some hurdles in his own way like writing other books in the middle of writing Reclaim.
  • Josh says he’s finished the rough draft of his book, but it has not yet been published. He’s put the draft in the hands of several beta readers and incorporated their feedback.
  • At one point Josh walked away from the book project, feeling a little burned out but also a little lost after an 18-month project came to a close.
  • “For probably 2-3 hours a day for 18 months I worked on that manuscript, and then for the last 8 months I’ve just kind of sat it down and walked away and re-evaluated where I wanted to take my career.” – Josh Duffney
  • Some of our previous discussions with Josh were around the concept of Deep Work. Is there a limit to sustained concentration?
    • Josh says yes. If you watch the people who have complete autonomy with their team, they will acknowledge there is a 4-hour maximum of creative output for most humans, whether it be coding, writing, or something else. You can be productive with other things (reading, digesting ideas, thinking), but we’re talking about work that requires extreme concentration.
    • Josh says for him 2.5 – 3 hours of deep work was probably pushing it to the max between getting up early and finding some time in the afternoon as well in addition to his day job. He tells us 90 minutes was probably the most sustainable amount of focused time he could dedicate to the book project when you add job responsibilities to life as a husband and father.
• When Josh was writing the nonfiction book he was doing technical writing for Microsoft as his day job.
  • Once he finished doing nonfiction writing in the morning he would go and do his work as a technical writer, hitting a total of probably 4-6 hours per day of writing.
• Is there a limit for maxing out deep work time on a daily basis for a long period of time (i.e. the 18 months)? In some way was Josh out of resources after that?
  • Josh feels if he had shifted focus he would have likely been fine. It may have been because he didn’t let himself see anything outside this specific project (the book), much like having on blinders. He got into trouble with career trajectory.
  • The time block specifically was very sustainable for deep focus, but Josh feels we should toggle on and off where your focus is during that focus time.

8:45 – Writing Processes and Shelving a Manuscript

• Josh had not written anything other than a technical book before starting this project. Along the way he learned a lot of lessons about writing in general like decoupling the different writing process.
  • When he began he was trying to outline, edit, and critique all while writing paragraphs. This was not sustainable, and Josh learned each needs to be done as part of a separate phase such as:
    • Collecting data and knowledge through research
    • Keep a roadmap of ideas in outline form
    • Some tend to just dive straight into writing the rough draft without outlining first. Josh tried both approaches (outline first and then rough draft vs. straight into rough draft).
    • Revise and edit or peer review
  • “You have to allow yourself time to get out what you’re thinking, and then you can go back through and revise and edit.” – Josh Duffney, on writing processes
  • Josh learned the processes mentioned above needed to be separated into different dedicated deep work sessions.
• Josh was instrumental in our adoption of the smart notes methodology (i.e. Zettelkasten). Did Josh continue using this process while writing the book since we discussed it during our last interview with him in detail?
  • Josh attempted it in various forms with varying degrees of success throughout his process.
  • He did use Zettelkasten at one point, adapted his own version of it, and used the PARA Method.
  • What Josh has carried forward now is an adaptation of these methods that works for him. The greatest benefit of leveraging these methodologies and adapting his own was a huge boost in comprehension.
  • The dream is to use the methodologies and wake up one day with a manuscript formed from it all, but that never really happened for Josh. Josh mentions Ryan Holiday, Luhmann, and Robert Greene as people for whom this may have happened.
  • Josh says he might have a collection of notes build up in a specific area that gave him confidence to write a chapter. When Josh went to go and write the rough draft, the material was so fresh in his brain in areas like these he didn’t need to rely on the notes as much as a crutch.
  • “It wasn’t necessarily that they were useless but that their utility was in solidifying my own understanding and building my own mental models that I could use to write….It was actually the act of writing the notes that was the biggest benefit and return on investment versus the artifact of the notes after the fact.” – Josh Duffney, on the utility of note taking for his writing
• It seems like Josh got lost in the subject matter he was writing about in much the same way that he got lost in his career. Was some of this because Josh was working on a nontechnical book this time as opposed to his pervious experience with more technical books like Become Ansible and How to Take Smart Notes in Obsidian?
  • Josh says he didn’t know where he was going in this case (i.e. no clear stopping point).
  • Nick says sometimes "switching things up " allows other things to process properly inside our brains.
  • Josh says he was like “a dog with a bone” when it came to working on the book Reclaim.
    • The author of How to Take Smart Notes mentions something about Nicholas Luhmann working on several manuscripts at once.
    • Josh would rather see something he’s committed to through to the end and struggles with switching tasks around like the above mentions.
  • Josh put down the manuscript of Reclaim for 8 months, and he feels it’s been relieving to do so. After recently being part of a Twitter space on writing that mentioned the Freewrite, he was inspired to pick up the manuscript again. For the past couple of days before this recording, Josh has been re-reading the manuscript of Reclaim and doing some revising.
    • If Josh had lowered his intense approach to writing and finishing Reclaim, he feels he might have enjoyed the process more and been able to focus more on where he wanted his career to go.
    • John says it’s hard to believe that we can successfully switch between multiple projects when we haven’t completed one yet (i.e. still working on a manuscript many years later but have yet to finish, etc.). Perhaps there is some kind of metric that can predict long term success of a project like productive words written toward a project, but we aren’t sure.
    • Josh learned that we need to toggle our goals when it comes to writing. Number of words written per day might be a great goal if you’re in the draft phase, but when you’re in the revising phase you are trying to remove words and should not use the same metric or measurement. There are overall indicators of project progress too.
    • Writing Reclaim was a side project, but Josh began to treat it like providing for his family depending on it, which drove up the level of intensity.
    • In Ultralearning by Scott Young, the author shares that there are extrinsic and intrinsic motivations for why you’re approaching something. Extrinsic projects (something you are doing for a reason outside yourself like money, etc.) work well with goals (words written if it’s a book, amount of time spent working on a learning course you’re creating, etc.). Intrinsic projects are for a personal sense of fulfillment and reward just by doing them.
    • Instead of looking at time spent writing his book as time spent on something he enjoys and considering it as something intrinsic, Josh switched to increasing the intensity and blurred the lines with the extrinsic motivations in trying to keep up with other writers like Don Jones. We need to match our goals with the type of motivation we have for the project in question.
    • John would add that we should consider our skill level and experience in the project area as well. For example, we might not write as many words per day as someone who has been writing for years.

20:33 – Energy Management and Long-Term Projects

• Knowing what he knows now, what would Josh have done differently on his work with Reclaim?
• Josh points out two things he would have done differently which could be applied to any side project like this.
  • Lower the amount of mental energy and time put into the project.
  • Take advice from movie producer and writer Kenneth Atchity. In his book A Writer’s Time he suggests taking 2 weeks completely off from writing anything every time you hit a milestone.
    • Josh told himself he would power through it. But taking the time off would have allowed the project to go on the back burner like we discussed earlier.
    • Atchity even broke down a writing schedule / agenda covering a 1 year period that included this 2 week break at every milestone of writing a book from start to completion. Without any breaks, Josh finished the book in less than a year.
    • Josh would write Pluralsight courses and would work on them for a 3-month period, for example but would add a buffer in between finishing a course and doing the next one.
  • “I didn’t put in those buffers. Any long project or any small projects that are linked should be spaced by a little bit of downtime.” – Josh Duffney, on integrating downtime
    • When we say downtime here it means switching off projects.
  • In the process of researching for Reclaim, Josh might come across interesting books (some technical, some financial, etc.) that were not directly related to the book. We would buy them for later reading but would not allow himself to even look at them because he was so focused on Reclaim.
    • For each dopamine rush of hitting a milestone, you will experience a low period from it. Josh references Andrew Huberman as discussing this (check out this podcast episode for more details).
    • During the 2 week break Atchity proposes between writing milestones is a good time to read books like Josh mentioned or pursue other interests to pick you back up or balance dopamine levels.
    • John points out how interesting it is to see that these patterns apply broadly across people.
  • Josh tells us the same thing happens at work and that we should not only think of this in the context of personal creative side projects.
    • After getting a big project completed and pushing it into production, Josh mentions the entire engineering team he works with is less productive for a week or two. This is often a time for the team to recalibrate, re-scope, and select the next project / milestone target and metrics. It makes sense in hindsight, but this is not something Josh initially thought of as something that could increase efficiency of he and his teammates.
    • Nick thinks this is really long-term energy management. In previous discussions with Josh, he shared how he managed energy over the course of a day.
    • John and Josh talk about how this lesson should be obvious to us (re-contextualizing after a major phase of a major project takes time and energy also) but that it is one you have to learn multiple times. John can see the pattern in himself in the past.
  • Josh really enjoys watching Kelsey Hightower talk about his different projects. Josh views Kelsey as someone who is both very ambitious and at the same time very kind to himself (a rare balance in people). For Josh, being ambitious at times has meant really pushing himself.

27:06 – Routines and Habits

• Nick mentions what happened to Tom Hollingsworth after finishing his CCIE as discussed in episode Episode 127 and wanted to know from Josh what it was like stopping work on a project he had spent so much dedicated time working on for so long.
  • Josh says it was a very restless time for him. In the Twitter thread about his career resurrection Josh mentions going through a thrashing period.
  • Right after the rough draft was finished, that is when the smart notes work started happening for him. The routine and energy was so ingrained in him (as well as the intensity and velocity), he ended up latching onto a number of things in succession:
    • For a while it was smart notes
    • Then he did some videos on YouTube (link to channel is here)
    • Then it became back to technology a little bit. But Josh wasn’t a site reliability engineer (or SRE) as he was during his Stack Overflow days.
    • Josh was a technical writer for Microsoft who was learning programming at the same time.
  • “…That habit just kept me propelled forward, bashing my head into walls, until finally all that energy kind of got spent, and I realized I wasn’t going anywhere. And I had to start to slow down and kind of re-examine.” – Josh Duffney
  • The re-examination happened right around the time Josh was able to move into his current role, which is a cloud advocate on the cloud native team inside Microsoft.
    • Fun fact – Josh mentions Steven Murawski (our guest in Episode 105, Episode 106, and Episode 107) is a teammate of his now!
    • Josh has reached out to a number of mentors to help him look at where he wants to go career wise.

29:25 – Lost in Thrashing and Purposeful Distractions

• How can listeners determine if they’ve hit the same career plateau Josh did and the are experiencing feeling of being lost?
  • As someone who has previously had pretty clear career goals, Josh can best describe himself during this time as being lost.
  • There are two parts to this conversation:
    • Persevere
    • Pivot (knowing when to do it)
  • A number of years ago Josh wrote a blog post called Be an Engineer.
    • This post described his journey to lift himself out of being complacent in his career. Josh then read Be the Master, which is now Own Your Tech Career by Don Jones, and it took him to that next level.
    • Then Josh hit another plateau 2 years later which we’re talking about today.
  • If your manager comes to you asking about your career aspirations but you have no clear answer, that is the time to slow down a little and evaluate what you would like to do instead of doubling down your efforts.
    • This is what had happened to Josh. He hit the senior track but knew he did not want to go into the manager track. Josh also tells us he was not entirely certain that he wanted to pursue the principal title as an individual contributor.
    • Sometimes we need to take time to evaluate what the potential next stages are. Josh is doing this right now.
    • If your manager is not asking you what you might like to do next in your career, you can still think about it on your own. Another good resource we would recommend is listening to Episode 45 on career conversations with your manager.
• Are there ways to bring one’s energy level down consciously or in a tapered fashion from a project milestone without the period of thrashing Josh describes?
  • Josh says his energy in terms of how he felt was about the same. It was the habit and momentum he had built which drove him to do the thrashing.
  • Josh has done a number of things to remove technology distractions from his life. During the 18 month period of writing the book, he had a light phone and not a smart phone, for example. Josh will also limit his screen time and does not play any games.
  • “One of the biggest reasons why I went headlong into that thrashing period was there were no distractions that I allowed into my life to actually diffuse that a little bit.” – Josh Duffney, on a period of career thrashing
  • Josh tells us about the concept of purposeful distractions. Excess energy needs a place to go, and habits need rebuilding. Some examples Josh has tried are:
    • Revising his workout routine
    • Getting out into nature more often
    • Going on longer walks
  • The above are very challenging habits to keep going, but in times when the excess energy needs a place to go, these have worked pretty well for Josh.
    • The “depression” book list we talked about earlier (labeled this way by Kenneth Atchity) is also an option for this kind of period. Josh tells us sometimes he’s not really in a place where he can read and needs something more centered on activity.
    • Josh tells us he would love to someday be the person who can just escape to nature and recharge if needed at any time.
  • Nick points out none of the purposeful distractions involved spending hours on Twitter each day (something Josh had struggled with a while back).
    • For Josh, the purpose of Twitter is networking, getting to talk to people he wouldn’t be able to speak to regularly otherwise.
    • Scrolling social media (Twitter or otherwise) would certainly be a mindless distraction, but it would not be very productive.
    • John mentions the social media scrolling would build up circuits of distraction and would not serve Josh well the next time he needs periods of sustained deep focus.

36:28 – Persevere or Pivot

• While still working at Stack Overflow, Josh received the Microsoft MVP Award, which was a decade-long dream of his.

• Even before this he landed the job at Stack Overflow as a site reliability engineer (SRE), which had also been something Josh really wanted for probably a decade leading up to getting it.

• Josh also finished his first self-published book, Become Ansible, around this time.

• The three events detailed above all happened within a couple of months of each other. Josh was about 31 at the time all this happened, and he’ll be 34 in October 2023 for time reference.

  • He knew there was a lot of runway left in his career. Josh started to wonder if he saw himself staying in the SRE role for a long time or moving to some kind of director role in the next several years. At the time he didn’t really want to pursue the director role as a goal in the next 5-10 years.
  • Then the opportunity at Microsoft to be content developer / technical writer came up, and after a lot of debate and uncertainty Josh decided to pursue this role at Microsoft and change disciplines.

• After Josh spoke to Jeffrey Snover on a Twitter space, Josh learned there are 2 types of transitions or pivots in your career.

  • One is visionary like Snover’s determination to see PowerShell through to fruition. He persevered and was determined to complete it.
  • Josh mentions at one point Jeffrey Snover joined the Microsoft Office 365 team as a technical fellow. It was an opportunity that presented itself. This was a chance to pivot and what Josh did by pursuing the role as a technical writer.
    • We also need know when it’s the right time to pivot. Josh had spent 18 months immersed in writing for his job and writing a nonfiction book.
    • The technical writing Josh was doing did not have as much of the problem solving type work in coding / programming, for example.
    • “I actually discovered that the problem solving itself was the more enjoyable thing versus writing, and writing was the side thing that I enjoyed. And so I had flipped where I get my motivations from or enjoyment and fulfillment from my work.” – Josh Duffney, on the realization of what he truly enjoyed in his work
    • Josh decided to pivot into something else that would allow him to do both things (problem solving and writing), and that’s when the cloud advocate role came up (which is sort of a 50 / 50 split between the two).
    • Josh didn’t see himself making a transition into being a long term successful nonfiction writer like James Clear for example, and he didn’t see himself in the technical writing discipline for more than a couple years. This took a lot of self-awareness to realize.
    • Josh remained a technical writer for Microsoft for about 18 months total before making a pivot to something else.
    • One thing lacking in the role as technical writer was coding / programming. Josh tells us the writing became a job, and he didn’t enjoy that job as much as he enjoyed his previous coding job or solving problems through coding.
    • The thing that Josh thought would bring him energy (the writing) began to take his energy from him.

• Josh tells us his decisions to pivot from SRE into technical writing and then into cloud advocacy may sound easy, but these kinds of decisions were not decisions that he took lightly. They were made very thoughtfully and carefully.

  • Pivoting is a very uncomfortable thing to do. You lose competence by moving into a new discipline and lose confidence. In that first full year as a technical writer it was pretty uncomfortable because Josh didn’t feel as competent as he had when he was a SRE.
  • Josh tells us this was like playing a video game with a character at level 70 experience out of 99 and then starting a new character. And you’re not back playing on easy. It’s more like playing on normal or hard.
  • The feeling was similar when Josh moved into developer relations (or devrel as he calls it). The career path in this kind of field is somewhat unclear and depends on a number of factors like who you are, what topics you focus on, how you are measured, etc.
  • Josh cites a phrase from The Technical Manager’s Handbook – “growth through ambiguity.”
    • At a senior level, a lot of the problems you should work on will be your responsibility to identify and scope. The organization is looking to you to find the problems and solve them. This is in contrast with Josh’s previous experience working the help desk where problems were pre-defined.

• Nick likes the video game analogy. With our previous experience in different roles it allows us to apply knowledge / concepts and recognize similar patterns in entirely new domains to define and solve problems. Did this happen to Josh?

  • Josh tells us we should seek to pivot our careers as close to our domain of expertise as we can, and he can testify to learning this the hard way.
  • Josh knew infrastructure and DevOps well as a SRE and used various configuration management tools and infrastructure as code tools in his work. When he became a technical writer, he started writing about the tools he had used such as Ansible and Terraform. This was a move into an adjacent discipline.
  • Then Josh became the lead writer for the programming language Go. He had no computer science background and had not learned any formal programming language. Josh knew PowerShell and some higher level languages pretty well, but there were some gaps.
    • This was a much deeper depletion of confidence compared to when he began in technical writing, and it took a while and a lot of energy for Josh to gain skills and expertise.
    • To gain experience with Go, Josh dabbled with web development. His prior expertise was in back end systems and not web development.
    • Josh found a path for himself in container security and attached it to his domain of previous expertise. There were a number of command line tools written in Go. Josh has 10 years of experience using command line tools and has many opinions about what makes a good command line tool. Josh’s focus now is on developing these command line tools (i.e. writing the code to build them instead of using them with scripts).
    • “Stay close to your domain of expertise and branch out. Then you can avoid a hard reset so to speak.” – Josh Duffney, on finding adjacent areas for his next moves
    • Another video game analogy is create a new character in the same account so you can give the new character “gear” to use. This gear would be items gained through previous experience.
    • Nick points out Josh’s excellent use of relatable experience which not many people are skilled at doing.
    • “If you can borrow from that domain of experience and you’re not completely starting over in a new account or whatever, you might be able to play on normal or hard core mode given your gear. That gear being the transferred knowledge of that existing domain you had prior.” – Josh Duffney, a video game analogy for relatable experience
  • John says there is something to having previous experience making a pivot that would allow you to recognize the discomfort and other things involved. We might call it an expertise in pivoting.
  • Josh says metalearning is a good term to describe this (re-skilling), and during the 18 month writing project for Reclaim, he did a research spike on metalearning. There are a number of great books in this domain:
    • Ultralearning by Scott Young as mentioned previously has good information on how to create a project around learning with a clear scope and end dates.
    • The First 20 Hours: How to Learn Anything…Fast! by Josh Kaufman talks about rapid skill acquisition and how to break things down.
    • The 4-Hour Chef: The Simple Path to Cooking Like a Pro, Learning Anything, and Living the Good Life by Tim Ferriss is another good resource. There is an acronym they explain in the book that speaks to how to break down components to identify what is most important to learn.
    • “Your ability to learn, your metalearning skills, and all the things in there like your ability to read and comprehend…will determine the rate at which you can pivot.” – Josh Duffney, on metalearning
    • A transition can force us to exercise these skills. It may be harder to pivot if we haven’t invested in some type of daily learning. Think of it as not letting muscles atrophy.

• Mentioned in the outro

  • We need to understand that people we look up to still go through struggles that are not so different than the struggles all of us face (sometimes on a daily basis).
  • We discussed the need for mental replenishment, and Nick recommends listeners read Rest by Alex Soojung-Kim Pang as well as Range by David Epstein if they have not. He cites these as 2 of the best books he’s read in the last several years.
    • Many of the ideas we talked about related to pivoting are aligned with the ideas presented in Epstein’s book.
  • The long-term energy management was interesting to Nick, especially after reading Charles Dickens and the Great Theatre of the World by Simon Callow and hearing stories of how depressed and drained Dickens would get after he did a public reading of his works or after participating in some type of theatrical production. It made Nick wonder if that was really depression or just a natural energy dip.
  • If you feel lost in your career like Josh did, you are not alone. You’re going to need to spend some time reflecting on the things you like and do not like about the work you do, and it takes time. There are resources available to all of us. It may be you need to hire a coach (and we have talked to many on the show) or speak to an unbiased 3rd party (a friend, spouse, family member, etc.). to generate some ideas. John says feel free to reach out to him to talk for 30 minutes if needed.
    • John emphasizes we have all been lost, and he’s been lost twice this year. We’re happy to share any resources we’ve found helpful.
    • Nick suggests writing or journaling to help do some of this reflecting (since we know writing is thinking).
    • This takes time outside your day-to-day job even if it’s for 15 minutes here and there or during a walk, for example.

Contact us if you need help on the journey, and be sure to check out the Nerd Journey Podcast Knowledge Graph.