Hi <<First Name>>,


It’s one of my favorite times of the year—spring is finally springing. In some ways, hope seems nearer. It’s Thursday to spring’s Friday, to the summer’s Saturday. And we’re almost there! 


Here are this month’s Best of Books recommendations:


You Are Awesome by Neil Pasricha


It’s been a few months since I first read Neil Pasricha’s book, and I’ve found its insights constantly boomeranging inside my head. “Different is better than better,” is one mantra of his that frequently pops up, a theme that’s intricately tied into the next book I’ll recommend. His two-minute exercise for making each day better is also valuable. Amidst the career advice, he weaves together very personal stories and cites psychological studies to create a compelling book very well-suited for modern times. By the way, if you like my newsletter, you’ll probably like his book recommendations too. 




On ongoingness: She told me she was just keeping her options open. Adding a dot-dot-dot to the end of the sentence. Letting things happen so she could navigate forward from a position of strength rather than feeling like all her doors had closed.


On facts vs. stories: Then we started telling ourselves a different story: "The fetus wasn't developing properly and a body is smart enough to know when it’s best to end a pregnancy." Did that tilted lens, this new story, take away all the pain? Of course not. It still hurt. Of course it did. But by telling ourselves a different story we moved away from toxic self-blame—and it helped us slowly move forward and move on.


On facts vs. stories 2: “I have one ball” is a lot different from “I'm disfigured with no chance of mating.” The first is a fact. The latter is a story. "I'm an alcoholic" is a lot different from "My family will never trust me.” “I failed my biology exam” is a lot different from “I failed my parents.”


On contemporary confession: It means that in our loud and chaotic world we need a place to let our thoughts clarify, congeal, and then fall right out of us. We get so bottled up. So tightly wound! We replay pains and problems so often, letting them swirl and spin inside us like tornados, that sometimes those pains and problems start feeling like who we are rather than simply what we’re working through.


On learning faster by working with companies that actually need help: And here I was sitting in front of the Dean who was telling me to set a match to it all. Ignore it completely and call up a pile of broken and bankrupt places.


I left that lunch and never applied for another job through the school again. Not a single info session, not a single job posting, not a single interview. I just went back to my apartment and made an Excel spreadsheet.


On the power of being different: At Walmart I found I was one of a handful of people quoting fresh research and case studies since I'd just read and reviewed so much at school. There was a ton I didn't know. I had no retail experience! No store operations experience! No Walmart experience! But the things I did know were different from what my colleagues knew.


And different is better than better.


One Person/Multiple Careers by Marci Alboher


Whether it's multi-hyphenates, slash careers ( generation "slashie"), a portfolio career, or the multi-path career, doing more than one thing is an increasingly relevant topic in the field of work. With the pandemic making remote work much more pervasive, as well as the changing meaning of work, this presents an opportunity for people to free up time that would require their presence at the office. One person even once took up two full-time jobs, one with Google and another with Facebook


I'd been deliberately positioning my career like this for eight years—since my senior year in college. I was a student with a full-time course load, working a part-time job with Xtreme Labs in Toronto, and freelance writing outside of that. Marci Alboher wrote the book I should have read when I graduated college, and that I want to recommend to everyone in transition points in their careers. I genuinely do think what we call a "slash" or "multi-hyphenate" career now, is going to be normal for everyone in the future. Even for people focused on a single career, this approach has implications for what Scott Adams might call their talent stack. Hat tip to my dad, who showed me the term “slash careers,” for this find:




On finding that perfect stable job: Finally, she realized that the way to end that cycle was to find a job that followed that rhythm—a job where she could work for a few months straight and then have an expanse of time big enough to get some of her own work done. It turns out that academia was the answer.


As Assistant Dean of Admissions for the School of the Museum of Fine Arts in Boston (where [Grace] Lisle-Hopkins studied), she works about thirty hours a week, accruing enough hours to take off all of January and then from June through August. 


On how to make slashes work: Recognize the value of the "virtual, portable, flexible" triumvirate. This strategy leaves lots of room to build a life comprised of multiple slashes.


On transitioning tasks to be more flexible: Think of column A activities as the Anchors, those things that require physical presence or are otherwise fixed in some way, and column B activides as the Orbiters, those things that can be done more flexibly. The key is to complement the parts of your life that aren't too flexible with activities that are flexible. If you try to combine too many of the column A Anchors, things can start to fall apart. Adding up a bunch of Orbiters in column B is usually more manageable…. 


Designating something as an Anchor or an Orbiter doesn’t have anything to do with its importance to you or its priority in your life; it just means that the Anchor’s logistics are more fixed than the Orbiter’s, or that the Orbiter vocation is flexible enough to be done around the constraints of the Anchor.


The beauty is that the moment you think of how to move something from column A to column B, it becomes easier to add something else from column A. For example, if you work as a C.P.A., that job will likely move from column A to column B if you start telecommuting and serving your clients via e-mail and phone rather than reporting to an office each day.


[Herbert’s note: Here’s what Alboher’s table looks like in the book. List out your different activities, based on how fixed or flexible it is.]


List Your Slashes

Column A: Anchors

Column B: Orbiters


On a common career flywheel: EIms’s career is also a model of what I call the teaching/ speaking/writing/consulting cycle, in which each slash fuels the others. Once you develop a body of knowledge, it's only natural to deliver that expertise to students, clients, and the public—and to do that means to take on these various labels.


On unifying vocations: If you can see the connections among your slashes, don't hesitate to connect the dots for others. Like many associations, once you lay them out for others to see, they have that of-course-they're-connected kind of quality.


On slash leverage: Examine the ways your slashes can distinguish you from others, give you an edge, or help you build relationships as you cultivate new pursuits. Always work to turn anything that could be a handicap into an advantage.


On slash synergy: Think about whether the training or skills you acquired in one vocation are transferable to another. Often, having multiple vocations can make you better at all of them.


Slack by Tom DeMarco


Slack is “the degree of freedom required to effect change.” This concept is key as more businesses and managers emphasize breakthrough creativity and innovation. Efficiency is the natural enemy of slack, because keeping people efficient—100% busy—means they have to process work before being able to address new work. This is fine for one employee, but if each employee’s lack of availability creates this lag, organizations tremendously slow down. Instead of considering slack purely as a wellness perspective, which is also important, DeMarco proposes that it’s an investment in an organization's own reinvention and human capital. As with all investments, a penny saved is not a penny earned. When stress is the problem, slack is the solution. I really enjoyed this book, and understood a lot more about why the way I approached and structured work was creating unnecessary stress. Whether you’re at a corporation or working for yourself, I’d highly recommend reading it.




On calmness: Very successful companies have never struck me as particularly busy; in fact, they are, as a group, rather laid-back. Energy is evident in the workplace, but it’s not the energy tinged with fear that comes from being slightly behind on everything. The companies I have come to admire most show little obvious sense of hurry.


On how availability affects speed: Think of it from the work's point of view: The time it takes to move entirely through the network is increased by each pause it has to make in someone's in-basket. If workers were available when the work arrived at their desks, there would be no wait and the total transit time would be reduced.


On mental shortcuts: So what's a useful shortcut for an efficiency expert who needs to show some quick organizational "improvement"? The shortcut that is most frequently employed is to assume that individual workers are entirely fungible.


On the cost of switching contexts: This ten-minute task-switching penalty is used up on the mechanics alone of the change: putting stuff away and taking other stuff out. 


On brainwashing by repeated assertion: The only method I have used so far to substantiate the 15 percent minimum penalty is a time-honored approach called proof by repeated assertion... Before I waded in, the presumption seemed to be that the task-switching penalty was essentially zero. ... Even without further proof of which of these two assertions is more likely to be correct, 0 percent or 15 percent, I hope you would feel at least a little bit uncomfortable with the 0 percent premise.



This month has been an exciting one. I covered the financial struggles that many creators at digital platforms face, as told through statistics from YouTube and Patreon. It’s a topic that’s incredibly relevant, with the emergence of the so-called “creator economy,” and more and more companies referring to its customers or partners as creators. Nearly 11,000 people have read it. If you’re a creator reading this, taking control of your income means owning your marketing and not outsourcing it to platforms.


In January and February, I recorded a bunch of interviews to talk about my book, There Is No Right Way to Do This. The first ones came out this month—one with Minimalism exec producer Jeff Sarris, another with clinical psychologist Nick Wignall on practical creativity, and one with ReadMoreCO. I also got to do an interview on the topic of personal infrastructure, which you can watch here if you like


For years, I’ve had friends, colleagues, and clients approach me about coaching. I typically bundled this service in with my projects at Wonder Shuttle, where I built and led my own team, as well as teams for organizations such as Intuit and Shopify. But I’ve always been curious—what would happen if I offered an individual coaching service that was public? 


A couple of weeks ago, I made this service available only to 10 people at an introductory rate of $100 per 60 minute call. 5/10 slots have since been filled. There are 5 more left. After that, I plan on pausing it and deciding what to do next. If I re-release it, it’ll be with more targeted positioning and increased prices. If this sounds interesting to you, you can learn more at this page. The password is “coachme”. If you want to talk about anything related to reading, learning, creativity, productivity, content marketing, or career planning, I think this could be interesting for you.



I hope that some of these passages unlock the hidden doors of your mind. Maybe some will serve as catalysts for change. And remember, they’re signposts. It’s up to you whether you want to apply them or not. Reply to this and let me know which quotes or books resonate with you, what you think of the newsletter, and if there’s anything I can support you with.




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