Exploring Leadership, Writing, and Personal Development with Bobby Powers | Glasp Talk #14
This is the fourteenth session of Glasp Talk!
Glasp Talk delves deep into intimate interviews with luminaries from various fields, unraveling their genuine emotions, experiences, and the stories behind them.
Today's guest is Bobby Powers, a dedicated learner with a passion for leadership and personal development. With over a decade of experience managing teams, leading onboarding, and Learning and Development programs at various startups and SMBs, Bobby is also an avid reader, having read over a thousand books in the last 15 years. He shares his insights through writing and public speaking as a top writer on Medium, where his articles on leadership, self-improvement, and book recommendations have reached thousands of people.
In this interview, Bobby discusses his journey into writing, which began in grad school when he started a book blog to share his favorite books with friends. He eventually transitioned into writing his content, inspired by a friend's encouragement. Bobby talks about his writing process, the platforms he uses, and the importance of iterative writing based on reader feedback. He also shares his thoughts on using physical and digital tools for note-taking and idea generation. He delves into his role as a Director of Learning and Development, describing how he helps train new hires, develop managers, and run programs for employee engagement and growth. Join us for an insightful conversation with Bobby Powers as he shares his journey, writing tips, and leadership philosophy, providing valuable lessons for writers, leaders, and lifelong learners.
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Transcripts
Glasp: Yeah, welcome back to Glasp Talk. Today we are excited to have Bobby Powers, a dedicated learner and teacher with a passion for leadership and personal development. Bobby has spent over a decade managing teams, leading onboarding and Learning and Development programs at various startups and SMBs. He is also an avid reader and has read over a thousand books in the last 15 years or so, sharing his insights through writing and public speaking as a top writer on Medium. Bobby's articles on leadership, self-improvement, and book recommendations have reached thousands of people. Today we will dive into the wealth of knowledge and experiences he has to share. So, Bobby, thank you for joining today.
Bobby: Yeah, thank you so much for having me. I'm honored to be here.
Glasp: Thank you. So, first of all, you know, you've been a writer for over 14 years, 15 years, right? And we'd like to know, like, what made you become a writer? You know, why did you start writing?
Bobby: Yeah, you bet. So back when I was in grad school studying for my MBA at Willamette University in Salem, Oregon, I was reading all these different books for fun. All my friends knew that I was an avid reader, and people would ask me for recommendations. I kept giving what felt like the same recommendations over and over and over—here are my favorite finance books, here are my favorite marketing books, here are my favorite books about leadership and leading meetings, and all sorts of things. I realized at the time that rather than just reciting the same list over and over, I should just publish a list online and create my own book blog. So I started running a website back then, and at the time it was just book reviews. It was basically business and leadership books, and I would write highlights of what I took away from that book and a little short summary or review of the book. Eventually, that morphed into wanting to write my own stuff. About, I think it was about seven years ago now, I was on a camping trip with some of my best friends, and my good friend Alex and I were talking about what we want to do in our careers. I had opened up to Alex and said, "Yeah, Alex, you know, I really want to be a leadership author and speaker. That's what I want to do." He asked, "Oh, well, what have you been writing lately?" And I said, "Other than these book reviews, I haven't actually written any of my own words yet." Alex, in his own very kind and gracious way, pushed back on me and said, "Well, Bobby, I don't know much about writing, but what I do know is that writers write, and I think you should probably start writing." That was the kick in the pants that I needed to actually start writing my own content. Shortly after that, I started writing articles and have now published hundreds of articles online, really getting a lot out of the process for myself and hopefully for others as well.
Glasp: Yeah, impressive. Did you start writing on, you know, you are a top writer on Medium, right? Did you start writing on Medium, or were you writing on your blog or website?
Bobby: Yeah, good question. So I actually started doing it on both. Because I already had this blog, I would publish my content on the blog, but then Medium allows you to crosspost the same kind of content on Medium as well. Medium is really where I focused my efforts for quite a while because it's a great place to quickly build an audience and connect with other writers and readers. Medium was definitely a heavy part of my writing. For anyone who's listening to this that is interested in getting into writing, Medium makes it quite easy because you have a platform with built-in user interface tools that make it quick and easy to write and publish.
Glasp: I see. But at that time, did you try any other platforms other than Medium?
Bobby: Yeah, I've looked into others and have published occasional articles with different publications or news magazines and that kind of thing. I know a lot of people use Substack today. I've checked out Substack a little bit, but it didn't seem like it was quite the right fit for me. There are many different platforms out there that are catered to helping young writers get started. Medium has definitely been the primary one for me, along with occasional other sites that reach out and ask me to post for them or start a relationship with them.
Glasp: Nice. And what's the differentiator of Medium? What is unique about using Medium for you?
Bobby: Yeah, good question. For me, it's really the UI/UX—the user interface and experience. That platform as a reader is very smooth and seamless. The way they do highlighting and commenting, actually like a lot of the different things that Glasp is quite good at, Medium started doing a number of years ago and really rose to prominence quite quickly because they made it very smooth and easy to save notes and to interact with other writers. That was the main thing that attracted me: I felt like it was equally good for writers as it was for readers. The fact that it was powerful at both of those things and had this community of people that wanted to learn and grow made it really attractive as someone getting started.
Glasp: I see. You mentioned that it's interactive, so part of Medium, but what kind of interaction are you using on Medium? Like the commenting or following, highlighting, what?
Bobby: Yeah, primarily the commenting. The commenting is great. If you publish an article on Medium, someone can comment and say, "This really spoke to me. I've already used these tips in my work, and thank you so much for writing this." That creates this community feel. I'll get those kinds of comments on what I write, and I will give those kinds of comments on things that I read on there. That starts a two-way conversation between writer and reader, which I think is very helpful and productive. The other thing Medium does that's really fascinating for writers and for anyone that wants to get started on a platform like that is that as the writer, you can see every section that a reader highlighted. I have some articles that I've written where I can see that one sentence was highlighted 50 times. Fifty people thought this sentence jumped out. As a writer, you then use that as an iterative process and sometimes write another article just about that concept. You go even more micro, focusing on this because it really jumped out to people. You use it basically as a testing ground; it becomes very iterative. You can see this jumped out, write an article about that, and in that second article, if something else jumps out, you go even deeper into that. So that's been very helpful for me as well.
Glasp: Yeah, and also as a reader, I often see, "Oh, this is the top highlight in someone's work," and sometimes that helps me see what most people are attracted to.
Bobby: Exactly.
Glasp: Yeah. And also, you are a top writer on Medium. You have more than 10 or 11 thousand followers on Medium. How did you become a top writer? Did some articles go viral, or did some topics go viral, or did your followers increase over time gradually? Could you share what happened and how you became a top writer?
Bobby: Yeah, it was a combination of all those things, really. One of the biggest parts is just to keep writing. I just kept publishing more stories, and I think that's the biggest one. So many people, myself included, when you start writing online, think that it's going to be very quick to get in front of an audience and build all these people, but it takes a long time. I've been writing on Medium for about six, seven years now, and it took a very long time to get up to over 10,000 followers and build all of this community that we talked about. One of the other things is that I was able early on in my time writing with Medium to land a couple different publications that I worked with, and I was able to do featured series with them. Early on, I did a series called Pro Tips, where every article I would break down the top 13 tips from one of my favorite writers. So I had articles that went mini-viral, sort of, from Stephen King, Malcolm Gladwell, Anne Lamott, and these different authors that I really respected. I would either watch their masterclasses or read their writing advice books and try to distill what I learned into 13 of their best tips and overlay my own stories and ideas and examples onto that. That featured series with this publication called The Writing Cooperative, one of the top publications on Medium, did really well. I'm really thankful to them for taking a shot on me as a newer author and really thankful to everybody who engaged in any of the different stories that I wrote on there.
Glasp: Wow, that sounds very interesting. I would love to check them out later. I see you were accepted into the Medium Creator Fellowship for August to October 2021. Did that help you become a good writer or write something engaging?
Bobby: Yeah, Medium is one of the platforms online that is constantly trying new things. They are always trying new programs to benefit writers, start up new publications, and constantly make their product better. That fellowship program was one of the things they did for a few months back a number of years ago, as you said. They would try to incentivize writers to write more content and be even more engaged on the platform. They had you apply to do that, and then anyone in that program would get additional tips, emails, and support from Medium. It was a way for them to also financially reward those authors for spending more time publishing the stories that they thought readers would want to know about. So, yeah, I'm thankful to have been able to get into that. Medium as a whole has been a great springboard for me in developing myself as a writer and trying to learn more.
Glasp: I see. In general, it seems like you're covering many topics. How do you come up with the ideas to write on? I mean, you are writing book reviews, which is your core writing topic, but what about other ideas like habit rules or something like "Being Over Doing"? How did you come up with these great ideas?
Bobby: A lot of it is just that I read a ton of books. You can see I'm surrounded by books here in my little office. I read a lot—over 70 books per year—because I love learning new things. I think it's so interesting to learn from the best ideas of all these different fantastic, brilliant people. Usually, the process is I'll be reading a book and it sparks a random insight in me, and I think, "Oh, I wonder how I could apply that in my own life." Then I sort of tweak it a little bit and a little bit more, and it becomes a catchphrase that I live by. The one you mentioned before, "Being Over Doing," came from reading David Brooks's fantastic book, The Second Mountain. The Second Mountain is about the idea that in all of our lives, we have two mountains that we climb. The first one is trying to be really good at our career—success, making money, and doing well in our job. But then after you hit the top of that mountain, you often see there's something more fulfilling out there that you're missing. You want to give back, help other people out, and that's the second mountain—giving to others. I read this book from David Brooks and thought, "That's a great concept. I want to try to live by that more." I tweaked it and put it into my own language, which was "Being Over Doing." We're all focused on doing, doing, doing—being productive and getting projects done. But being is way more significant. Being is about what kind of person you are, who you want to be in the world, and how you want to show up for friends, family, and significant others. So this concept of "Being Over Doing" really stuck out to me. It was sort of a tweak on the David Brooks concept and a way that helped me remember it a little bit better. Then I started to write about that, and thankfully, that was one of the articles that ended up catching on with a lot of people online.
Glasp: I see. Also, regarding the two mountains, there are two of my favorite quotes: "Sharing is caring" and "Knowledge is power." Combining them, "Sharing knowledge is empowering others." I love this concept and the second mountain—giving back to other people, society, and the community.
Bobby: Yeah, I love what you said too because those two simple phrases, when they're wed together, are so powerful. You could build a life on those two phrases—building knowledge and sharing that knowledge with other people. I think it's so cool what Glasp has been able to build to help people do that. Any tools that allow people to build knowledge and share knowledge—I'm forever indebted to.
Glasp: Thank you, thank you so much. You like a lot of concepts or ideas, but where do you keep ideas to write next?
Bobby: Yeah, there are two primary ways I do it: one is physical and one is digital. For me personally, both are very important. For physical, in every single book that I read, I underline and put notes in the margins. I use the back cover of every book as a storehouse of all my favorite tips and ideas from that book. Let me grab an example here and show what this looks like. In the back cover of this book, The Coaching Habit, I have a one-page back cover summary of all my favorite tips. If I haven't read this book for six years, I read it in November 2018. If I want to refresh my memory, I open up the back cover, and I have the page number of every one of these tips and a one-sentence or a few-words summary of what was in that book. Then a few other different key things or recommendations from that author that I wanted to try in my life. That's one way; physical is very helpful for me. I read physical books, take physical notes. The second way I do it is digital notes. I use Obsidian—I love Obsidian. I have an article on BobbyPowers.net about how to use Obsidian as a complete beginner, as your second brain tool. For anyone unfamiliar, Obsidian is a personal knowledge management tool, an app that allows you to save notes, tag those notes, and connect all of them to each other. It's similar in some ways to Glasp, Roam Research, and Notion. I've used Obsidian for quite a while to take my notes from a book like this, put them into digital format, save the quotes, save the stories, and tag them. Then I can later use those as a writer. If I'm writing an article about how to ask better questions, I can pull up my tag "questions" in Obsidian and pull in all the different resources that I've saved for that. It makes writing way easier for me, speeding up the writing process probably two to three times.
Glasp: I see. I like it. The back cover concept or back cover idea to keep your memory is like your pinned article on Medium. This simple technique helps get more out of every book you read.
Bobby: Exactly, it's that story.
Glasp: Thank you. I like it. You mentioned that you read physical books. Do you read Kindle books or only physical books?
Bobby: I only read physical. I'm a little bit weird in that way. I tried reading digital books years ago when Barnes & Noble came out with the Nook. I was a big Barnes & Noble fan, so I bought a Nook Color, spent $250-300 on it, and started reading on the Nook Color. As I was talking to friends about what I had just read on my Nook, I realized I didn't remember any of it, even if it was just one week prior. For me personally, the e-reader just didn't work. I wanted something physical that I could take physical notes with, but I also wanted the power of digital search. This helps me pair both—I have the physical notes in the physical book and back cover and margin notes, but then I save the best ones into a tool like Obsidian, and now it's searchable and I can find it easily.
Glasp: After you read a book and take back cover notes, do you put everything into Obsidian as well?
Bobby: I will, yeah. I'll put all of the best notes into Obsidian. In the back cover of any book like this, there might be 30 some notes. I'll usually put anything that's that type of high-level note into Obsidian, along with my favorite quotes from that book. It takes a little bit of time, but it's helpful because it also helps me refresh my memory on that content. Maybe a week after I finish the book, I'll go and write those notes up.
Glasp: It makes sense. Many people read physical books and take notes, but it's not online, so they cannot search which book a concept is from. I remember the concept but not the book. That habit of putting all the concepts and ideas into Obsidian is pretty good. You mentioned you've tried Obsidian, Roam Research, and Notion, but what made you choose Obsidian?
Bobby: I did a lot of initial research on those three. I didn't try each one robustly; I just did research online and read about how people are using them. One of the keys for me is that Obsidian saves all of its notes in standard markdown files, basic text files. I don't want to be wedded to one specific platform. Some of my friends have used Evernote for years, but Evernote has a custom file type. If you ever want to leave Evernote, you're stuck because of the custom file type. I wanted to use markdown files or a more global standard file type that I could take with me if I ever want to go to a different platform. That was one big deciding factor. I also really liked the interface and usability of Obsidian. It felt like a dev writing code almost, which appeals to me. I'm not a dev, but the concept of seeing notes in that format and tagging and connecting them in an integrated way appealed to me.
Glasp: Yes. I love the concept of not being tied down by a specific platform. How do you keep track of the books you want to read next? Do you use Goodreads or something else?
Bobby: Goodreads is the main tool I use. I've tried a lot of different tools over the years, different custom apps, but couldn't find one that did what I needed. Goodreads is the closest fit. I've made it a little bit specific for my use case. Goodreads has a "to be read" list, which for me is hundreds of books. There's only a small fraction of those books that I actually plan to read soon or want to buy a copy of soon. I have different tags—not only "to be read," but also a custom tag called "to buy." "To buy" has maybe 200 books, and "to buy soon" has a maximum of 30 books. For someone like me who reads a lot, I needed to filter the 600 some books down to what's most important now, based on what I'm going through in life in the next few months.
Glasp: Interesting. I have a lot of books I want to read in my Goodreads or the Japanese version of Goodreads. It's never finished.
Bobby: I know, yeah. If we ever finish our book lists, it probably means we're dead.
Glasp: You mentioned custom tags like "to buy soon." Do you have any advice on making filters? What are the criteria?
Bobby: That's such a good question. I honestly still struggle with that. One filter I decided to use this year is coming up with a theme to guide my reading. This year, my theme is reading about the past and the future. I'm reading a lot of biographies and history books, but also things about AI and nanotechnology. This theme has helped me zero in more. I'm reading books that inform my understanding of the world and how we got here. For example, right now, I'm reading a book about the American war in Vietnam, a very sad and moving book called Kill Anything That Moves. It's about the extreme injustices America committed in Vietnam. It's a book that I wish didn't describe such horrible things, but it's fascinating because it's part of our history and something we have to own up to. So, this theme helps me zero in. For those looking for a way to decide what to read next, I'd say come up with a theme and read about a specific topic. The author Ryan Holiday talks about the idea of swarming a topic. If you want to learn about the Civil War, for example, read as many books as you can for a couple of months about the Civil War—novels, historical books, biographies, people's journals. Swarm the topic from all these different perspectives. I'm sort of doing my own version of that in my reading now.
Glasp: I see. Do you do book clubs to polish your ideas or get more out of the books you read by exchanging ideas with other readers or writers?
Bobby: I do, yeah. I have a few different book clubs I've been in through the years. The longest-tenured one is a group of about half a dozen of us that meet once a month. It started at an old company I worked at, and we've been meeting for years even though we all left the company. Only one person is still at the company, but our book club continues. We rotate who does book recommendations, so sometimes it's fiction, sometimes non-fiction. It's just whatever the pick of the group is for that month. That's one group I'm in. I also have a book club at work right now that meets quarterly at my new company. I have a friend, my buddy Thad, who I meet with frequently to talk about what we're reading. Right now, we're reading a book called The Power Broker about Robert Moses, who helped build a lot of the landmarks and infrastructure of New York City. Thad and I meet occasionally to talk about different books like that and choose a new one each time we finish.
Glasp: I see. When you're reading or writing, people are using chat or AI tools nowadays. Do you use AI for brainstorming or to understand more about the book or writing? Is it part of your workflow?
Bobby: I haven't used it too much for anything with writing or reading. I'm a little bit leery of the tool for writing because it's replacing so many different roles with writing. There are different articles on Medium that have been shut down because they were written by a language model tool. But I have used it for practical things like planning a trip to Paris with my wife. I used ChatGPT to help come up with a travel agenda, put it in a spreadsheet, find restaurants to check out, and get information on open and close times and costs. I've used it for that but haven't used it much for reading. Some people use models like ChatGPT to summarize books. I've tried it a little for that, but the danger is thinking you're getting all the insights when you're not. The insights aren't just in the summary; they're in the stories, the deep examples, and the human connection in a book. So for me, AI is helpful in some fields, but it's been misapplied in others, like summarizing and thinking you got the core idea enough when you probably didn't.
Glasp: I found an interesting point that people think in stories. Stories help people remember things. As you mentioned, the summary or insight itself is helpful, but people forget after a week or so.
Bobby: Exactly. I even get the same question with books that I write the book summary on my own website. I'll write a summary of the biggest takeaways for me, and I'll occasionally get comments from people saying, "This is really helpful, thanks for writing the summary. Do you think I still have to read this book?" The answer is, "Well, yeah, it's a 250-page book that has so much depth and insight and wisdom. You should still read the book. I just gave you the very, very tippy top of the insights that came out to me, and it might be different insights for you." Knowledge isn't passed through just pithy statements; it's passed through the emotion, the feeling, and the story. If I read someone's summary that has a one-sentence explanation of a topic, like the book Atomic Habits, great book, fantastic book. If I read someone's one-sentence summary about what an atomic habit means, I'm not going to learn much from that. If I read James Clear's explanation for why atomic habits are important and why we have to do small chunks of a habit to actually adopt the habit, now it's sinking in deeper. It strikes the emotion and core more in me, making me more likely to actually do that. Summaries can never fully substitute, and anytime we look to them to do more than they can, it's a big disservice to ourselves.
Glasp: Totally agree with that point. Sorry, this is a little bit different topic, but you've been in the position of Director of Learning and Development at several companies. I'm curious about what that role is and what kind of job and responsibilities you have. Is it related to reading and learning or a different kind of learning and development?
Bobby: It's definitely related. I would describe my job as helping train new hires, develop managers and executives, and run programs for all employees to feel connected to our company and constantly learning and growing. Those three buckets—new hires, managers, and everyone across the company—are the broad categories. We run programs for all of them. We just finished up a new manager boot camp at my company, Jitasa, where we have employees across five different countries and brand new managers trying to figure out how to lead for the first time. We did three days of Zoom calls and trainings with all these managers together, talking about different things they need to learn as new managers. That's one example of the kind of program I do. Every time we have new hires, we run them through specified training about our core values and the company, which are very important to us. We train new hires about their specific roles and how to do bookkeeping and accounting for nonprofits. We run programs like a talk series called Jitasa Journeys, where we talk about each person's career story—what journey they've taken in their career, what they've learned so far. The audience is everyone, whoever wants to join can join and learn about the career story of our COO, Director of Client Services, or whoever else we're interviewing.
Glasp: I see. Is it common for companies to have Learning and Development (L&D) roles? I've never talked to someone in that position before, so I'm curious if it's common.
Bobby: It's becoming quite a bit more common. Fifteen years ago, the role didn't exist in many companies. In the last 10-15 years, more companies have seen the need for it. They realized that if employees don't feel they're growing, they leave the company. If you're not investing in these people and creating a career path for them, they go somewhere else where they are being invested in. More companies, especially newer, fast-paced tech companies, have seen the need for L&D roles. They realize, "Let's get in front of it, be proactive, and hire someone to focus on the needs of those employees and train, develop, and coach them in a better way." I'm glad the role exists, but just like you, it took me a long time to realize there are people doing L&D.
Glasp: Is it related to HR?
Bobby: Yeah, normally it sits within HR in most companies. HR was a position I never thought I'd want to be in. At past companies I worked at years ago, I thought I could see myself in any role except HR. It seemed like it was about compliance, legal stuff, protecting the company, and not very people-forward. But then I realized that HR in a lot of these more people-first tech companies was actually a great place to be, especially if they had L&D roles that I could step into and help people feel more engaged and connected with the company.
Glasp: Thank you for explaining that. You teach leadership to managers, right? What kind of characteristics or skills do leaders need to learn to be good leaders?
Bobby: There are unfortunately so many things. If I were to whittle it down to a few, one of the biggest things is to exhibit confident humility. It's a phrase I think about a lot. You have to be both confident and make decisions, but also recognize you might be wrong and be humble and look for ways to grow and improve. Confident humility is really important for managers of all sizes and any tenure. Make decisions in your areas of strength, and if you have an area where you feel weak or don't know enough, rather than blindly making a decision and exposing your people to a bad decision, ask questions. Ask your team, "What do you think we should do? I don't know a good answer to this, what do you think?" That balance of confidence and humility is really important. I would also say courage. Managers have to speak up and say the unpopular thing. One past boss and mentor of mine, James, used to say, "You should say the one thing that everyone is afraid to say because that's probably what needs to be said in this meeting." A manager's job, a true leader's job, is to share feedback, share ideas, and challenge authority when needed. I've had plenty of times where I've had to do that in different positions when I've disagreed with someone higher up in the company.
Glasp: At the same time, changing mindset is really the hardest part, similar to changing identity for some people. How would you encourage people to do so? How should they evaluate if they're doing well or not? Do you have metrics to follow?
Bobby: Such big questions today. It's really hard, like you said, changing identity is very difficult. It would be way easier if I could say, "As a new manager, just take these classes and you'll be good." Unfortunately, it's not like that. A lot of it is core heart skills, becoming a better person, someone others want to follow. That kind of change can only happen if you're actually getting feedback from others and are open and receptive to that feedback. One thing I always coach our managers to do, regardless of whether they just became a manager or have been managing for a long time, is to ask for feedback in one-on-ones. You're probably giving them feedback, but you should also be receiving feedback. Ask, "What can I do differently as your manager? How do you feel I could improve in leading our team?" If you open up your heart enough to actually hear what someone's saying, that can pierce through and change you in a different way. It's a tough thing, for sure, and there's no silver bullet for it. There's a phrase from a movie I watched a long time ago: "There's no silver bullet, we're going to have to use a lot of lead bullets." You have to use a lot of small changes because there's no one big quick change. For new leaders, it's asking for feedback, reading books, personal development, and looking for ways to open up yourself to be more open to coaching and changing how you lead.
Glasp: Definitely. I know some people take things personally and become defensive when they get feedback. They need to change that gradually.
Bobby: I have trouble with that too, even to this day. If I get feedback, my gut reaction sometimes is to be defensive. What I try to remind myself and our managers is that whenever you get feedback, the first thing out of your mouth should be "Thank you." It's simple but very powerful. Saying thank you calms you down a bit and puts you in the headspace of being grateful that this person had the courage to share. I sometimes even say, "Even if I don't agree with some aspects of this, and we can figure out the best solution, I'm so thankful you told me because I know it takes a lot of courage to say that." Thank you for doing this, now let's try to figure out how to make this better. Another key is to sit on the same side of the table with them to solve the problem, rather than seeing them as an opponent. This person sharing feedback and ideas is not the enemy; they're actually on your side, trying to help out and make you better. That's a great and powerful thing.
Glasp: Thank you, thank you so much. Do you have any book recommendations for first-time or second-time startup co-founders?
Bobby: You definitely are not asking for personal experience, are you?
Glasp: I want to, yeah, just in general.
Bobby: One of the best books I found is Startup CEO by Matt Blumberg. It's a book where every chapter is about a different element that you need to know as someone founding a company. It covers everything from legal forms, hiring employees, creating core values and company norms, creating an employee handbook, finding product-market fit—everything from operations to HR to legal and compliance stuff. I've recommended it to past friends of mine who started companies, and they found it really helpful.
Glasp: You mentioned Matt Blumberg.
Bobby: Yes, Matt Blumberg, I believe.
Glasp: I'll check it out. At the same time, this is a random question, but Kei has read 4,000 books in his life. I read, not as much, but every time I read books, it energizes and motivates me. I thought I learned a lot from the books, but when I go back to work, I can't apply what I learned. If I can't apply it, did I really learn? How do you close that gap? Do you have any advice?
Bobby: There is a big gap between those two. One way the back cover helps me is that in the back cover of a book, I'll often have a section that says what I want to do differently with this information. I'll have a bullet-pointed list of different things I want to try. The faster you can apply one thing from that book, the more likely it will actually bleed into you and what you're doing. In the back of these non-fiction books, I'll have a list that includes things like "try doing this in the next meeting I lead" or "ask this kind of question in a retrospective with the team." It might be "launch this project." Reading with a lens for what can I apply today or tomorrow and putting notes in the back helps hold yourself more accountable. This isn't just a good hypothetical idea; this is a tactic I'm actually going to apply in my toolkit today.
Glasp: That's really helpful advice, thank you. Our audience includes aspiring writers and readers. Do you have some advice for those starting to write, like how to become a top writer on Medium, and habits or rules to make their life more effective?
Bobby: What I would start with is the advice my friend Alex shared with me: writers write. That's the biggest impediment for most aspiring authors. They think they have to have all this knowledge before they get started. You don't need to have knowledge before you start. You should just start writing today, whatever you're passionate about, and publish it. It's really scary the first time to hit the publish button. I remember my first Medium story, which wasn't great, but it doesn't matter. I was almost shaky hitting the publish button. I had one of my best friends and my wife read over the story. I was so nervous. Write and publish, but also give yourself a lot of tolerance and grace. You're going to make mistakes. I've heard the advice before and think it's fantastic: if what you're writing today doesn't disgust you two years from now, you're not growing fast enough. What you write today should not be very good when you look back two years from now because you should be getting better every day, every year. I write with that lens. I may not be proud of the story a year from now, but I'm proud of it today. This is the best story I can write today, so I'm going to publish it today. When I look back at it a year from now, I think, "Oh, I would have written that differently. I'm a better writer now than I was then." That's great; that's exactly what you should be feeling because you should see growth and evolution. Another good book out there is Steal Like an Artist by Austin Kleon. It's a very short little book, about 150 pages. The whole genesis of that book is that the best writers, artists, poets, and musicians are all taking ideas from other people and packaging them in their own way. Rather than that being bad, it's actually good. That's how art works. You need to credit your sources and thank those people, but you should steal like an artist. If you read something that really inspires you, write about that, share that, and put it in your own words. Try to come up with a better, more meaningful way of saying it that will connect with the next reader.
Glasp: I love the quotes from Steve Jobs: "Creativity is just connecting things," and "Connecting dots and packaging." Also, "Someone's work is someone's footnotes," right? We are putting footnotes to each other. I love that concept.
Bobby: I love that quote you just said. I don't think I've heard that: "Someone's work is someone else's footnote." That's fantastic.
Glasp: Yeah, I love that too. This is kind of the last question, a little bit heavy. Glasp is a platform where people can share what they're reading and learning as their digital legacy. What kind of legacy or impact do you want to leave behind for future generations?
Bobby: The best answer I have to that would be that I want to help people become better leaders, learners, and communicators. That's a commitment I have on my blog, BobbyPowers.net. These are stories and articles for people who want to be leaders, learners, and communicators. If I were to leave any legacy, it would be that by reading what I've published, there are more leaders out there in the world, even just one more leader, better communicators, and people who can do these things in a slightly better way than before. That would be the biggest answer to that question. Another way I would like to impact people is by focusing on not someone else's definition of success but your own. Write your own path, your own definition of success. I think about a young college student named Sean that I was mentoring years ago. Sean was trying to decide between different career paths—grad school, an internship opportunity with a company that partnered with Starbucks, or going back to his home country in Africa to start a business with friends. He was trying to decide between all these different things and asked, "What's the best path?" We had a rich discussion about legacy and success and what he wanted to do with his life. What he landed on, and what we landed on together, is that success isn't one box to check. Success is not a role or a title. I used to think I wanted to be a CEO someday. Horrible goal. No one's goal should be to be a CEO arbitrarily. A better goal is to ask, "How do you want to impact the world? How do you want to help people out?" Rather than aspiring for a position, I realized I want to aspire for a life impact goal. What impact do I want my life to have on other people? For me, it's helping people become leaders, learners, and communicators. For Sean, it was something a little different. For each of you, it's something a little different. But we have to be crystal clear on what that is. Why are we on the planet? What are we here for? It's not to make money or arbitrarily be a CEO or climb a career ladder. Dump the career ladder; focus on something meaningful.
Glasp: Really beautiful and insightful advice. Thank you. Thank you for joining today's talk. We really enjoyed the conversation.
Bobby: I did too. It was great to spend time with you both. Thank you again for having me.
Glasp: Thank you, thank you so much.
Follow Bobby Powers on social:
- Website: bobbypowers.net
- X: @BobbyPowers_
- LinkedIn: @bobbypowers1
- Article: Use This Simple Technique to Get More Out of Every Book You Read
