Free Time with Jenny Blake

I’m delighted to welcome Daniel Doyon to the pod this week, co-founder of one of my favorite software services, Readwise. Every morning while I have my coffee, I look forward to checking out the daily email roll-up of five serendipitous snippets pulled from my entire library of Kindle highlights. In this conversation, we cover: how Dan and his cofounder handled the famous “hug of death” from Tim F...

“Business, like life, is all about how you make people feel. It's that simple, and it's that hard.” —Danny Meyer, Setting the Table Danny Meyer is a famous restauranteur responsible for founding some of my favorite spots, including Gramercy Tavern, Eleven Madison Park, and the popular Shake Shack chain. He pioneered the philosophy of “enlightened hospitality.” That’s the thing about engineering su...

“You are making a choice every time you undercharge.” How’s that for a splash of cold water to the face?! Bad pricing strategy puts your business—and your body—at risk. As today’s guest, Erin Haag says, when your prices are too low, “You are choosing to work an additional 10, 20, or 30 hours per week to generate the income you need to survive.” In this conversation, Erin shares what led to two hos...

🎉 This week marks the one-year bookiversary of Free Time making its way into the world, and the two-year podiversary of launching this show. 🥂 As I reach these milestones, a question looms: Has the book writing, launching, and marketing been a success, as I would define it? In today’s solo, let’s ride the mindset rollercoaster of launching something new into the world, and I share specific one-y...

“How did you go bankrupt?" Two ways. Gradually, then suddenly.” —Ernest Hemingway That’s the kick-off quote from returning guest Khe Hy’s recent pivot-in-progress big reveal, taking us behind the scenes of his business in a recent post titled, “The $645,099 business pivot.” Khe is the founder of RadReads and former Wall Street managing director. Khe returns to the pod today (as our first three-pea...

Free Time. The phrase connotes, leisure, fun, time off, vacation—as if we're skipping through meadows with butterflies! 🦋and unicorns!🦄 But if you’re a long-time listener, you know that I think of free time as a verb. It is a skill, a muscle we can build. Freeing Time is something we can get better at. By creating smarter systems and taking small steps today, we can set our time free far into th...

“What’s the highest level I can serve?” That’s one of the driving questions that today’s guest, Melissa Hughes, helps business owners answer while building companies and making an impact on the world with grace and ease. She believes that the more of us who can shine our lights unapologetically, the better off we all are. In this conversation, Melissa shares how she knew it was time to leave corpo...

Feeling slow, stuck, uncertain, or in the midst of a morale dip? If so, today’s minisode is for you—or for a business bestie who might need a little pick-me-up. I share a surprising shift from an encounter with Serendipity Signage; a portal to gratitude on a random New York City train station wall under a set of shattered windows.  When you feel down, remind yourself (as I do) what Julian of Norwi...

Stephen Shapiro is a quintessential Free Timer. Throughout his 20+ year self-employment tenure, he has run a variety of experiments to optimize for freedom and joy. To name just a few: working one hour a day (for years!), clearing space for 15 weeks of travel and/or vacation each year, and week-long hotel stays for focused work sprints.  We also talk about the “existential meltdown” that led to a...

One of the biggest lessons I learned from author Nassim Taleb is that whenever he finds himself bored with what he’s writing, he stops. His logic? Surely if you are bored as the author, your readers will be too. Taleb takes it as a sign to drop that direction or concept altogether unless he figures out a way to get excited about it again.  In Free Time, I share a similar sentiment: how we bake is...

How do we use technology to facilitate real relationships? That’s the big question driving Gina Bianchini’s epic entrepreneurial quest. Today we’re talking about the magic phrase that will transform what you’re building, the difference between social networks versus social media, why a course is not a community, how to avoid working too hard as the host, and why you might benefit from building a s...

How many times have you gone skidding into vacation, arriving exhausted from trying to “earn” it before you leave? Then feeling guilty for any loose ends you were unable to tie up in time, maybe even brooding the first few days because you’re so burned out that you aren’t even enjoying your precious time off nearly as much as you thought you would?  Research shows that we can experience diminishin...

Here are a few food-for-thought reflection questions, inspired by today’s guest: Are you working with amateur clients or ones who bring out the best in you? Are you pricing the “aggravation factor” into your proposals when necessary? What about “throwing proposals over the fence,” creating self-inflicted stress when prospective clients ghost you as a result? Finally, are you stuck in the feast-or-...

You’ve probably heard the phrase, “A book is a business card.” That’s because what you don’t hear is that a book is a wonderful revenue generator! It isn’t — at least not directly. The extreme Time-to-Revenue Ratio of writing and marketing a book is not for the faint of heart, unless the book connects directly to a larger part of your business model, serving as lead generation for more profitable...

Prolific punchy pontificator Khe Hy—creator of the $10K work accelerator and Supercharge Your Productivity—returns to the pod to share his strategy for collecting inspiring content, repackaging interesting tidbits, and regularly hitting “publish” on his newsletter, RadReads.  Today we’re talking about idea kernels: micro-ideas that can be elaborated upon and turned into different kinds of content...

Should you self-publish? This is a big debate among aspiring authors, and there is no one right answer. Today I’m sharing my take on the three main publishing options you have to get a book into the world:  Self-publishing (including direct-to-ebook or audiobook) where you hire your own team of specialists along the way. Hybrid where you partner with an established publisher, while fronting the co...

Processing email and social media inboxes is overwhelming enough for one person — can you imagine creating an entire company to help entrepreneurs do this at scale?! Communication curmudgeon that I am, I most certainly cannot. That’s why I invited today’s guest, Yaro Starek, to share the systems and approaches behind Inbox Done, his company that helps clients tame the never-ending email beast. Mor...

Do you ever feel like you’re just not good with systems? If so, then this episode is for you. The more efficient we can be in our operations, the more time we can set free. Today, I’m sharing five questions to keep in mind while working to increase your awareness for potential automation opportunities. Automation is a skill, and this episode will help you get better at it. For more help and inspir...

Juggling a schedule for one person is tricky enough; for a two-entrepreneur household with kids, it’s another thing altogether! Learn how Jess and Dave make time for each other, for themselves, and for their deep work in today’s conversation about creating free time together as a family. More About Jessica: Jessica Marati Radparvar is a social impact strategist motivated by the belief that doing t...

One of the most common questions from those accessing the Author Toolkit (an assembly of my best-open-sourced templates and processes from 14+ years and three books) is a variation on: How can I decide on a topic? How do I narrow down my idea? How do I know if/when I have landed on the right idea? Today I’m sharing ten filters to help you narrow down your book idea — or, if you’re not an aspiring...

What type of business would you build if you no longer needed the money? After a life-changing exit from her previous company, Meet Edgar, Laura Roeder’s answer: a fun one.  She is now more focused than ever on building a business that is bootstrapped, agile, asynchronous, joyful for all involved, and powered by part-time team members who love what they do. In this conversation, we discuss why Lau...

I had high hopes for the first couple of weeks of the year, but I rang in 2023 in bed, completely uninspired by goals or ideas—anything beyond a desire to get healthy and feel human again, let alone any loftier business aims. Taking a (very loud) hint from the universe, I settled on the theme THRIVE as my focus to start the year. One of the most common replies to my “wave a magic wand and fix one...

What’s the right thing to do, and how do we do it quickly? In this conversation with Strategy Sprints founder Simon Severino, we cover: Why you shouldn’t start with your ideal avatar; setting daily, weekly, and monthly strategy planning (and measuring) habits; how he scales his business through certified Strategy Sprints® Coaches; creating self-healing loops, and greater resilience by tying roles...

As I shared in last week’s solo episode, Free Time isn’t about time management or productivity, or even simply doing work more efficiently. It is about setting time free.  If our time is trapped like a bird in a cage, unless we break free of shoulds and obligations, there it will remain. We achieve this through smarter systems, and that includes getting better at saying no.  My own tendency to say...

Imagine my surprise when, on the Saturday before I was set to be interviewed on a podcast last summer, my phone dings. It’s Door Dash. Huh?! I didn’t order anything . . . Turns out it was a surprise delivery from the producer of that show, Matthew Thompson. Next thing I know, my husband Michael and I are enjoying iced coffee and yummy treats with our Sunday morning reading—I have never felt so tak...