If you’ve been in the entrepreneurial space for more than a hot minute, you probably know Charlie Gilkey. He started out with a blog, but now he is the creator of Productive Flourishing, a podcast and a site that helps people do the work that matters so they can become their best selves. Believe it or not, we nabbed Charlie as a guest on Worth It, and we’re really excited to share this interview with you. So, let’s get to it.
00:40 Who Charlie Gilkey is — and why we’re so excited to chat with him!
01:40 Charlie’s background as an Army logistics officer
03:23 How he took his first blog to a full-on business and podcast
03:43 Why his new book, Start Finishing, is different from other productivity books out there
04:46 Charlie’s view of the “bro” productivity literature that currently exists
06:19 Why our focus on work (rather than our lives) is a crisis of priority
07:40 The hamster wheel so many of us find ourselves on
09:15 Why money is an instrument, not the end goal
11:10 What happens when you add intention and purpose to your money
12:16 How to make more space for those projects you want to finish
12:57 What “thrashing” means
13:51 How most of us are going about “finishing” the wrong way
14:20 The 5 Projects Rule
15:25 Why choosing what you’re NOT going to work on frees you to start finishing
16:49 The 2-Hour Rule
18:15 The risks of not scheduling in your project-based work
20:35 Why we tend to justify economics but not emotions when we outsource our work and lives
23:15 The idea of “Project World”
24:35 What Charlie means by “No date, no finish”
28:30 The problem with to-do lists (and how we use them)
30:05 The 15-second or 2-hour decision you’ll need to make with each to-do list item
31:01 The 3 ways we experience time
33:23 Why we run and hide when we don’t have our projects properly aligned
34:23 The risks that come with thinking motion means progress
35:29 How to take back your time by being mindful of your device use
37:58 The risk of planning too far in advance
41:05 Why Charlie often recommends that entrepreneurs don’t plan for more than 6 mos out
42:43 How to handle multipotentialite tendencies
43:10 The benefits of finishing something at a level of mastery
47:39 Charlie’s mission in life
While most of our conversations center on money and how to build wealth, we know that most of our audience are entrepreneurs who have multiple interests, love exploring new business ideas, and who want to make the most of the time they’re working. After all, you started your own business so you could have time to do what you love, right??
And yet, as Charlie talks to us about in this episode, we tend to prioritize work to the point of sickness or burnout, and we do it all in the name of money or “getting things done.” The result is that many of us feel like we’re just working for money, that we’re not in alignment, and we don’t have time to do the things we really want to do — or even need to do.
Charlie goes into detail on why this is in his new book, Start Finishing, and he was nice enough to shed some light on this during our chat. In fact, he calls it out pretty early in this episode: If you’re struggling to find the time to do what you want to do, it’s not because there’s not enough time. It’s because your priorities aren’t aligned.
We all have busy lives. It can feel like we’re running from one thing to the next, trying to get ahead. And it can feel like a hamster wheel. We’re not really getting traction and we’re not doing what we feel most called to do because, you know, you have a lot on your plate.
But let’s be real. You get to choose what you’re working on — and what you’re not working on. It can be hard to change what you’ve already set in motion (yes, you have to finish that client project or get those meetings done before you can really make space for what’s important to you), but you can set yourself up for success starting now. How? Charlie calls is the 5 Projects Rule.
This rule is one that Charlie highly recommends, especially for those in the entrepreneurial space. Basically, it means no more than 5 projects per time slice (a day, a week, a month, a quarter, a year). Many of us have 5+ projects we work on in a day, like “Do the laundry, finish that work project, mow the lawn, do the groceries, schedule the vet visit, figure out the water bill” etc. — and it’s no wonder we don’t have time! We are literally cramming our day with projects. Instead, Charlie recommends cutting it back to 5. 5 a day, 5 a week, 5 a month, whatever it is. But no more than 5 in a time slice. To do this, you’ll need to figure out what you don’t have to do, or what you can delegate. Get real with it, and don’t let other people’s priorities or emergencies affect this once you’ve made a decision. Stick to your project plan!
And if your time slice is bigger than a day — a week, month, quarter, year, etc. — you can break those projects down into smaller time slices. In a really good planning world, Charlie says, you’d have a long-term project chunked out into smaller projects, i.e. a month-sized project broken down into week-sized projects.
If you’re wondering how to break down your projects by week or even day, Charlie has a recommendation for that, too.
Ask yourself what a 2-hour chunk looks like for your project breakdowns: what can you get done in 2 hours and where you can fit that block of time into your schedule? Charlie also shares that you can ask yourself which items you can get done in 15 minutes, because you knock things off your list really quickly when you see those things come up.
He also adds that we all underestimate how long it takes to get stuff done, so build in a buffer! For a rough buffer, Charlie says you can multiply the time you think a project (or work block) will take by 3. So that 15 minute project… it might actually take you 45 minutes. Plan accordingly.
Charlie shared his big productivity secret on this episode: “No date, no finish.” If you don’t have a date for that big project you want to finish, or that little project you want to start, it’s never gonna get done. And picking a date is only half the battle. From there, you need actionable breakdowns — those 5 projects per time slice we talked about. What are you doing today/tomorrow/this week/this month to move you closer to that goal?
There’s another important point that Charlie made: we tend to run and hide from our commitments to our own projects. How often have you stared at your to do list, started to write that email, or tried to find information about your new pet passion… and froze? Maybe you ran straight to a client or customer issue to resolve, or you decided to open Instagram, or maybe you buried yourself in email busy work. #Guilty
But the problem with this is: We trick ourselves into thinking “At least we did something.” But it isn’t the work you should be doing, and you know it. So get real with yourself, make a plan, and make it actionable.
This is just the tip of the iceberg in terms of what we talk about in the podcast. Charlie also covers the problem with how we all manage our to do lists, the risks with planning more than 6 months at a time, and more. We talk about all of it in the podcast, we but we also talk about his new book: Start Finishing.
While this is technically a “productivity book,” Charlie says it’s different in three ways:
He hopes to help people thrive in their businesses, homes, and communities, and we think he’s well on his way. If you want to know how to finally start finishing, juggle all of your many interests, and create a schedule that lets you do more than work and feel guilty… this episode and Charlie’s new book are perfect for you. Check them out!
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