“I’m always stumping quarterly planning for business owners. It’s the Goldilocks horizon for strategy execution, project scoping, and team alignment.” Today I’m talking with Charlie Gilkey about why the quarter is an ideal time unit for strategic planning, how to apply his stepwise Momentum process to mapping projects and goals, and striking the balance between visioning and planning. Charlie also had an interesting response on why tracking metrics matters . . . and it’s not what you might think.

There is a chicken-and-egg problem in the early days (and transitional moments) of any business: you need to earn more money in order to hire help, but hiring help is one of the only ways you can free your time to do the highest revenue-generating activities. Today I’m sharing the best investment I made in Q1 of 2022, even though it wasn’t a direct line to profitability (but pretty dang close).

Don’t bother starting a {business, blog, podcast}, the market is already too saturated! That limiting sentiment gets thrown around a lot—not least of which by our own mind. But just as there is always room to make new friends, so too can you find your best fit audience.

This week Megan Dougherty, co-founder of One Stone Creative and host of The Business Podcast Blueprint, takes over the pod again to share the benefits of podcasting, even within a seemingly-saturated topic.

If you’ve been in business for more than a few years, you’re probably well-versed in the perils of switching costs and shiny object syndrome when it comes to trying new software, especially if there’s a high learning curve.

Today I’m sharing more context on a conversation I’ve been having repeatedly behind-the-scenes with people who are curious about switching to Notion for their business operations, but a little hesitant to make the time and energy investment. I share three reasons I am grateful to have made the switch: functionality, simplification, and customization.

What are your business goals for your current or potential podcast? If you are like many business owners, you may not have set them set in stone before getting started. Today’s episode is the first of two crossover episodes from Megan Dougherty, co-founder of One Stone Creative, a podcast production agency, and host of The Business Podcast Blueprint. I asked her to take over the pod because I loved this advice so much! Listen in to find out what the three high-level company podcast archetypes are, and how they will help your business :)

How valuable is your time? Are you conveying that value to your potential clients? In the first five years of running my business, I spent way too long thinking I was the only one who could handle important communications with current and potential VIP corporate clients. Taking inspiration from Cyrano De Bergerac, today I’m sharing a mindset and process that enables a team member to take on the heavy-lifting of client communications.

“If you build an audience, you can figure out how to build a business.” That has been the guiding mantra behind Brian Clark’s pioneering business-building throughout his career. He is someone I’ve long admired, from his early days founding Copyblogger to his many new ventures. Today, we’re talking about building the audiences that make it all possible.

There's so much energy and attention that swirls around during a launch, and I cannot thank you enough for helping create the momentum that we did!

I've talked a lot about launching with ease and joy, generating magic and serendipity, not muscling through book marketing. I’ve also talked about sprinting through the finish, and the overwhelm that comes from wanting to give a big creative project every last drop of energy to help it succeed. Today I’m sharing my strategy of sending the first 1,000 serendipity seeds out into the world.

“Brain science teaches that even if a prospect knows, loves, and believes in a company’s offerings, after they become a customer, fear, doubt, and uncertainty will plague their thoughts.” That familiar feeling is buyer’s remorse—and if you’re not building systems to directly address it within customers’ first 100 days, you are far more likely to lose them.

Today we have a favorite time-saving strategy from listener Liron on keeping a Mess Page at your desk to free your mind during deep work sprints.

Now that Liron has kicked off this series, I encourage you to submit your favorite time-saving tip so that we can all continue learning from each other and freeing time together!

Leadership and org design always involve tradeoffs. Which ones are you willing to make? Are you building traffic lights in your business or roundabouts? Do you want to maintain power and control, deriving identity from your role, or are you interested in exploring and creating a self-managing organization where there is no CEO?

Today we’re talking about the new wave of Decentralized Autonomous Organizations (DAOs), bolstered by the blockchain, but something Aaron Dignan has been practicing for over a decade.

Just a few days after launch, Free Time is already topping many Amazon charts . . . although "making the lists" is not something I lose sleep over, it does go a long way toward raising awareness and generating lasting launch momentum.

In Free Time, I share operating principles to help you run a more agile business. Each chapter is a call to action—ways of working smarter, teaching ourselves and team members to operate with greater joy, ease, and efficiency.

Thank you all so much for the incredible book launch support this week!! Because of you, Free Time is topping the Amazon charts!

Today my friend Antonio Neves hosts part two of our launch week conversation (listen to episode 077 first if you haven’t already). In this second half, we’re talking about evolutions in business and personal revolutions in parallel. This is diving deep into the real personal realm, and it is the most vulnerable I have been in over six years of podcasting. I am so grateful to Antonio for holding this space, and to you for listening—I hope it serves you in some way.

I love mastermind groups, and how they create the space to support and learn from fellow business owners. They come in all shapes and sizes, paid and unpaid, and illuminate ideas and questions we might not always find simply from reading books and attending conferences. Today, I’m sharing some of the forms these groups can take, and how you can initiate powerful small-group connections with other professionals.

Today kicks off another exciting chapter of life and business because the Free Time book is officially out! There’s no one I’d rather hand over hosting duties to than my long-time friend, fellow author, and podcast host, Antonio Neves, to take the lead on this celebration conversation. We’re talking about creating art, investing in yourself, and the incredible journey of going all-in on something you’re passionate about.

Without conscious reframing, launching can quickly tip toward stressful. Writing and launching a book is a privilege, so I hesitate to harp too much on how hard it can be. Whenever I feel stress climbing, I remind myself to find the joy and ease, to reconnect with gratitude for that exact stage of the process.

That said, launches still have a way of snowballing stress! Today I’m breaking down seven reasons why, and five strategies for reducing the inevitable stress at the edge of a major—and majorly rewarding—challenge.

Have you fallen out of love with something in your business? Something you want to be doing in theory, like sending newsletters, but you’re hitting a wall of resistance? In this episode, I'm coaching a long-time friend and founding BFF community member, Wade Brill, through the Free Time Framework. Wade is also featured as the kick-off story for the Align stage of the book.

If the thought of success sometimes feels more stressful than exhilarating, you’re not alone. Many business owners are interested in scale only if they’re not scaling stress and headaches at the same time. In fact, some even subconsciously hold back from earning more, fearing that any more income might bring with it increased headaches.

What if this is the moment that changes everything? That question can be exhilarating or terrifying—or both. And there are going to be moments like that in your business: crossroads where you have to make a choice. Today’s guest, Pat Flynn recently made one of the biggest decisions of all, to step aside as CEO of his company, while still playing an active role, so he could devote more time to the creative work he loves.

Going from “zero to one” on a big creative project can be intimidating. If you want to write a book or create a course, where should you begin? Hint: grab a pen and paper and a stack of index cards, not your laptop.