Sept. 25, 2025
Breaking Down Your Work: A Strategic Guide to Outsourcing and Automation
Ever feel overwhelmed by your to-do list? That sensation of drowning in tasks while your most important work gets pushed aside? You're not alone—and there's a solution hiding in plain sight.
In this eye-opening episode, Jesse breaks down a deceptively simple framework for identifying exactly which tasks in your life and business should be automated or outsourced. Using a visual "bucket and drops" system, you'll discover how to categorize your work, break large responsibilities into manageable components, and analyze frequency patterns to make strategic delegation decisions.
What makes this approach different isn't just the practical methodology, but Jesse's candid acknowledgment of the real barrier most professionals face: "The solution for getting comfortable with the idea of outsourcing or automating is reps." He shares personal examples from his own podcast production journey, revealing how he transitioned from doing everything himself to focusing solely on the interviews while delegating all other aspects to his team.
The brilliance of this system lies in its scalability. Whether you're considering hiring your first virtual assistant or looking to reclaim hours each week through strategic automation, this framework provides a clear path forward. Jesse offers specific tactics for getting started, including how to use AI tools to identify automation opportunities and how to begin with lower-risk monthly tasks if you're hesitant about letting go.
Ready to stop doing work that others could handle better? Want to invest more time in developing your unique gifts? This episode delivers the practical roadmap you need to make it happen. Listen now and take the first step toward working smarter, not harder.
Check out the Video for all the details
Learn all about the Self First Framework
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00:00 - Introduction to Automation and Outsourcing
06:30 - Understanding Your "Buckets" of Work
12:28 - Breaking Down Tasks into "Drops"
17:58 - Podcast Example: Tasks to Delegate
22:28 - Reflection and Frequency Analysis
25:48 - Getting Started with Outsourcing
28:08 - Using AI Tools for Automation
WEBVTT
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We are going to be talking about how to figure out what to automate and what to outsource.
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What I got for you, actually, is a super simple way to like figure out what those things are, and I'm just going to kind of flash this bad boy up at you right now.
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We're going to dive into my Trello board and we're going to get into what are the buckets, how many drops, or what are the drops that are in the bucket, and then how many times do they happen.
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This is how we kind of tease it out and peel apart the big giant tasks that we have, that we do all the time that we could like outsource or automate so we could spend more time investing in ourselves.
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I'm Jesse, and the stuff that I share here on these live streams and on the socials is the tips and tricks that took me from the field to like actually operating my own business, which is a little crazy.
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And the reason I share these things is because I want to help you spend more time working to leave this industry, this world, your teams, your communities better than you found them.
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Like I said a little while ago, we're going to drop into the buckets.
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And what do I mean by buckets.
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I'm kind of super big overview when I'm talking about buckets.
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I want you to think about colors, right?
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Or buckets first.
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What are the things For me?
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I've got a podcast.
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I've got work like my growing my business.
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I got personal.
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I've got publishing.
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I've got work like growing my business.
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I've got personal.
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I've got publishing.
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I call it publishing, which is just like blogging and writing.
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And then I've got other things, but generally that's where I spend, oh, and then administrative right.
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So generally that's where I spend my time.
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When you're thinking about buckets, I want you to think about where are the large chunks of spaces that you spend your time in?
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That is what qualifies as a bucket.
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And then, when you think about drops in the bucket, within each of those buckets there's a bunch of little things, a bunch of little steps that fill the bucket right.
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And so we want to like tease out what are the buckets first, and if you've already done this phenomenal, let me know in the comments what are your buckets, and then we're going to tease that apart.
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And then, once we tease those things apart and we do some reflection and that's why the tool is important, because the daily domination board is the method or the mechanism that helps me see all of these things and that's the critical point is being able to see, visually, see and reflect on.
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What are all the elements, what are all the buckets?
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Where am I spending all of my time and breaking it up If we don't have it like, if it's in our head, it seems like this big, one, singular thing, and if it stays that way, we will never be able to like, automate or outsource the thing.
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All right, folks, so let's jump into it.
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So what are your buckets?
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Think about this Like right now brainstorm.
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It's not a test.
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I'm not going to grade this bad boy and I ain't going to tell on you, but drop it in the comments.
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What are the buckets that you spend most of your time in?
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And I'm going to kind of start high level and say work home, marriage, right, whatever those buckets are.
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Start thinking in those terms what are your buckets?
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And let's go to the fancy Trello board.
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So this is my like.
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You don't have to do it this way, I promise.
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I know this is probably going to seem psychotic to a lot of people out there, but that's the way I roll and so, visually, you can see the different colors here.
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Those are my different buckets, and so for yellow, it's administrative.
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It's administrative stuff that I have to do invoices and emails and schedules.
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So that's one bucket.
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Then I have the orange bucket, which is relationship building and industry committees.
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Right, that's me being involved or engaged with other human beings that aren't necessarily like a business or a service that I got to deliver, a product I got to deliver.
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It's just maintaining connection and contributing as much as I can to the people I care about.
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Then I have this red one, which is curveball and social marketing, and if you were here at the last live stream, we talked about the curveball, so we're not going to talk a lot about it today.
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You can go back and watch the replay.
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And then purple, and so I'm going to spend a lot of time talking in the purple bucket here because it's the most granular.
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I think that might paint the picture that we're talking about.
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So purple is my podcasting bucket.
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It's all the little tasks that are associated with me scheduling, recording, producing, posting a podcast.
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There's a bunch of drops in there.
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Then I got blue for real estate, I got green for publishing, I got pink for me, self-care and skill building, and I got this kind of black gray bucket and that's all things related to my business.
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And so I'm going to ask you guys again what are your buckets?
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Hopefully, or if this ain't making sense, let me know.
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First step, step one what are the buckets?
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Where do you spend most of your time at?
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Get those out of your head, write them down, scribble them.
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You don't need crayons to do it, just get them out of your head, like, think about what are those buckets, what are the things, the areas that you spend most of your time in.
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And then, if you're using the Trello board or you can do it on your calendar I like Trello because it's my love language Then you can assign colors to the thing.
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Right, and the main value for me in assigning colors to it is so that I can visually see and identify what bucket am I playing in.
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Again, this is to help us tease out and filter through the big giant, monumental things that we deal with on the regular and see it in a more granular level, because this is going to set the foundation for what do we automate and what do we outsource.
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And why do we want to automate and outsource?
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It is so that we can spend more time developing our gifts and talents and share our gifts and talents with the world, because that's the only way we're going to make it better the world, because that's the only way we're going to make it better.
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Let's go to the comments.
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Craig says I manage my finances in buckets, so why not organize my time better?
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Also, oh, I love that.
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Okay, craig, thank you for throwing that out there.
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What Craig, to the point to like figuring out what I can automate and outsource, is more about the thinking than it is the stupid tool that I use.
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I use the tool so that I can see it visually, and it's a habit that I've had for I don't know, probably a decade now, using the Trello board and the mural board and all the things that I use, anyway.
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So, craig, thank you for throwing that out there.
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It's what are the separation, where the boundaries may be, between the different commitments that you have or the different things that you're involved in.
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Write those down, then assign them a color.
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I like colors, again, because it's super duper visual.
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So, Craig, thank you for that.
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My brother and so we talked about identifying your buckets.
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Now, after you've identified the buckets, I want you to pick one right now If you didn't write them down.
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Write them down.
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Write down a few, two or three or four buckets where you spend most of your time.
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Like I said earlier, you can keep it simple, work home easy.
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There's probably a whole lot more that you do.
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Pick one of those buckets and now what we want to think about is what are the drops in the bucket?
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Right, because what does a bucket do?
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It collects water, it collects fluid or whatever, but it gets filled.
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My buckets get filled with a bunch of little drops of things, a bunch of and in terms of like this, this idea of drops I'm talking specifically about, like the steps or the little tasks associated with that big bucket.
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So let's go back to the Trello board and so you can see here the drops in my bucket and we're going to look.
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I don't know if y'all can read that.
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Maybe I don't Let me know if y'all can read that, like, if the um, uh, whatchamacallem, if those little the cards are, if they're clear enough to read, cause maybe I want to keep them secret.
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But anyways, what I want you to like focus on is the purple color, right, this range of purple.
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That bucket is my podcast bucket and so when I first started doing my podcast the learnings and missteps podcast, that switch podcast I had no idea how much time it was going to take and how much work was involved.
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But I did it weekly.
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Well, at the first, at first I did it like every other month, and when I do it on that frequency it's kind of hard to see.
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I just knew it was a lot of work and it was going to take, you know, three to six hours for me to go from interviewing to posting the thing right.
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Why?
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Because I timed it.
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But as I got into repetitiveness, right as I did it, the more reps I got, the clearer I could see like, oh wait, this is a separate.
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It's all in the same bucket but it's a separate task and it's things that I needed to schedule out.
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And it was also able.
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I was it enabled me to see that I don't have to do it all in one shot.
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I could like break it up.
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And so back to this, back to the tool, back to my buckets.
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You can see here there's probably more that I can get into, but that's not the point.
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I've got episode art and publish, so I got to create some episode art so that I can upload it and publish.
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So that is one of the drops in the bucket I've got do the interview, right.
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What does that mean?
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I have to interview amazing people, or I get to amazing, super amazing people, two amazing, super amazing people.
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Then I do a cut in the intro and the outro of the thing, right.
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Like I have a little teaser at the beginning.
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Now I'm talking about this in present tense.
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I don't do most of this stuff anymore.
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I used to do all of it and then it's produced.
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So produce for release.
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What that meant was to edit the stupid thing, qc check is listen to it after I've done the editing and it's right before I publish it.
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And then another drop in the bucket was research, podcast, guests and, like I said, those could be broken down even smaller.
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The point is, when I started decided that my podcast and this could be anything that you have in your world.
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It could be your workout routine, it could be, it could be your finances.
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Like Craig, I think this is a beautiful example.
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Craig says financial management, document control, hr, self-management, curve balls, meetings oh, those are the labels.
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That's what I'm talking about, baby Nice.
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So there you go.
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You got a template that you could use from Mr Craig.
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Thank you, my friend, that's freaking awesome, okay, so so back to the thing.
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I first started by saying I have a podcast bucket and originally that purple card was just podcast.
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But over time, because I could see how often it was happening, I was like man, maybe I need to break this down.
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And because I had a bucket for it, I was able to start thinking about what are the little elements within that bucket, and so you could see there's one, two, three, four, five, six we're not going to count broadcasting, because that's actually what I'm doing right now is live streaming, right?
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So there's six steps in my bucket.
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Those are the drops within my bucket.
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Now the question then becomes is like so what, jess?
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You keep talking about buckets and drops in the buckets.
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I thought this was about automating and outsourcing.
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Ding, ding, 100% accurate.
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And so, by getting granular, right to like diving into the weeds of the thing, I was able to identify.
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Because here's the thing, here's a secret.
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Nobody tells you, right, we all talk about automating and outsourcing and how amazing it can be, and you know, value your time or nobody's gonna value you and all of this stuff.
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I I agree with all of it, by the way, but it's super hard, not because of, like, articulating the steps and all that.
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You got freaking chat GPT.
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Now that could do that for you.
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It's hard because I had to release control comfort with inviting someone else into my space to do the work that I so earnestly spend hours upon hours obsessing about, and so I don't.
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The solution for getting comfortable with the idea of outsourcing or automating is reps.
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I don't know any other one.
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So if you're out there in the omniverse and you have like a super simple trick that helps you really come to terms quickly about outsourcing stuff or automating stuff, let us know in the comments, because I've seen the people that I've worked with, folks that I've coached.
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That is the biggest hurdle for them.
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It's not necessarily figuring out what or how to outsource, it's coming to terms and becoming comfortable with the idea of somebody else doing the thing.
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That's super hard, but anyways, that's a little extra bonus there.
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I don't even know where that's coming from, craig, I'm going to blame it on you.
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When I did my buckets and the drops of the bucket, I was able to see okay, I've got a whole bunch of little things in here.
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I've got the episode art.
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I got the interview to do, I got the intro and outro, I got the produced edit, qc, research.
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That's a lot.
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And then it was a simple question that I asked myself Of all of these things in this bucket, which are the ones that no one else can do, that only I can do?
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And this isn't new knowledge, right?
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This is a fundamental thing when we're thinking about scaling and growing our business, or outsourcing work, et cetera.
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And guess what?
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The only thing on that list of all of those drops that no one else can do was the interview.
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Now, I'm sure you're probably like well, anybody could do an interview.
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Yeah, you're right, but I want my face in the podcast too, right, so I wanted to physically be there.
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But the scheduling of it, the research of the guest, the production, the editing, the episode art, the cutting in of the intros and outros, I don't have to do that, and there's plenty of people out there in the world that have the skillset and love doing that.
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And so that's where I started Like, like for real, for real.
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Ms Kayla, if you're watching, you're amazing.
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Love, all the help and relief that you bring to my life.
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I got me a personal assistant and I knew that I needed to get his personal assistant.
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If y'all know me out there, I'm not the easiest to get a hold of and my response time isn't always the greatest, and that was just.
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That was why it's like, okay, I need to deliver a better service, so I need an assistant so we can like close that gap.
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I evaluated like, okay, what are the things that I can give that are like low risk, that happened on a high frequency, so that we can get good at it, and then we can build on that.
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And it was the podcast.
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And so now the only thing I do well, I still do the scheduling.
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I'm working on that I'm working on, but so I do the scheduling and I do the interview.
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Everything else is done by Renee at Duran styles, uh, editing, and miss Kayla, who who does all the other finishing touches and makes it amazing and makes the images and puts the things out there.
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But I never would have gotten to that point if I didn't understand my buckets and I didn't understand the drops in the bucket.
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And so, quick review we're going to talk with the first two main points and then we're going to get into the third point.
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But the first two main points is what are your buckets?
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Think about that, write it down or drop it in the comments.
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What are the buckets?
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Where do you spend most of your time?
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Family, friends, working out, church?
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We all have different things that we're committed to, the little projects that you have.
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Do you work on vehicles?
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Are you building a hot rod?
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Whatever those are, those qualify as big buckets.
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And, in thinking, within those big buckets, start breaking them down, because that's where the drops in the buckets are and those are the things that drops in the bucket, the steps that are associated with those big, bigger things that you're doing.
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That's where the ideas or the things to automate and outsource are going to come from.
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I'm going to give you another real quick example.
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I don't really like going to the groceries because I don't like standing in line and I get rude and it's just.
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It's just not.
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It's not a fun experience for me and it's a bit somewhere between two and three hours every week for me to do that, and you know, in particular, about my produce.
00:16:54.131 --> 00:17:07.939
But I had to let go of that and so I outsourced it, because those two to three hours, sure, I'm paying, you know, a few extra bucks for it, but those two to three hours I can invest in other things, relaxing.
00:17:07.939 --> 00:17:19.224
I could give some more attention to all the people out there in the omniverse all the make it happeners come up with new ideas, whatever it is, but most of all, it helps me conserve my energy.
00:17:19.384 --> 00:17:25.377
So maybe, if you want to like early start, get the things, the tasks, the chores right.
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This might be an easy key for you.
00:17:26.932 --> 00:17:38.939
Get the chores that you do on a regular basis, that's easy Laundry, housekeeping, lawn work, maintenance on the vehicle, grocery shopping, like get creative with this.
00:17:38.939 --> 00:17:45.865
All of those things are things that you can outsource or you can automate right, depending on how you look at things.
00:17:45.865 --> 00:17:55.465
Now, if you're out there and you're like, okay, I've hit it, I feel like I hit a ceiling.
00:17:55.465 --> 00:18:03.469
I've been progressing, I've been making things happen, I've been getting things done, but I feel like lost or I feel maybe a little empty.
00:18:03.469 --> 00:18:06.241
Or, like Scarface said, is this?
00:18:06.241 --> 00:18:08.749
It Is this what I've been working for?
00:18:08.749 --> 00:18:17.030
I got you the Self First Time Mastery Workshop is coming up and in that workshop, we're going to deep dive into all of these things.
00:18:17.099 --> 00:18:26.784
What we're talking about on this call right now is just one, one element from the daily domination practice, which is, you know, managing your execution on a daily basis.
00:18:26.784 --> 00:18:44.732
We ain't even touching on the strategically selfish scheduling or guilt free future planning, and so if you're looking for an edge to like, get more time back and just feel fulfilled whenever you do everything or anything that you want to do, you got to sign up for that bad boy.
00:18:44.732 --> 00:18:46.484
So drop self first in the comments.
00:18:46.484 --> 00:18:47.888
If you're interested, I'll give you the link.
00:18:47.888 --> 00:18:49.181
If not, that's all right.
00:18:49.181 --> 00:18:53.088
Come back for the next free live stream, all right.
00:18:53.189 --> 00:19:09.105
So now that we've talked about what are your buckets and what are the drops in the bucket and you really, really want to get a return on your investment, what you want to do is evaluate, and this requires some reflection.
00:19:09.105 --> 00:19:11.150
All of this is going to require some work, y'all.
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I know some of you probably think like oh, my God, I got to create all these cards and I got to do colors.
00:19:15.550 --> 00:19:18.948
It's like, yes, yes, it requires work.
00:19:18.948 --> 00:19:21.737
Or just keep doing what you're doing.
00:19:21.737 --> 00:19:25.651
If you're completely fulfilled, satisfied and operating to your optimal potential, keep doing what you're doing.
00:19:25.651 --> 00:19:29.726
If you're completely fulfilled, satisfied and operating to your optimal potential, keep doing what you're doing, because there's other ways to do it.
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This is just the way.
00:19:30.462 --> 00:19:31.185
I know how to do it.
00:19:31.185 --> 00:19:39.632
But if you want a different experience on this world and you want to contribute to a greater degree, my recommendation is you try some of this.
00:19:40.093 --> 00:19:59.016
We did the buckets, we gave them colors, we broke down the drops in the bucket, all the little steps associated with those things, and so now we have a framework or a template to use whenever we're scheduling our work and scheduling our task or going into the daily domination board and doing the thing.
00:19:59.016 --> 00:20:01.144
So here, let me do this Right.
00:20:01.144 --> 00:20:02.729
So we got daily domination.
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That's what we're doing today.
00:20:03.951 --> 00:20:06.162
Do this right.
00:20:06.162 --> 00:20:06.804
So we got daily domination.
00:20:06.804 --> 00:20:07.666
That's what we're doing today.
00:20:07.686 --> 00:20:17.538
The trick to figuring out and identifying, pinpointing the thing that'll bring you the greatest value, is all about reflection, which takes us back to why coloring the thing is super, super helpful.
00:20:17.538 --> 00:20:20.569
We're going to go to the done column and once a week I do this.
00:20:20.569 --> 00:20:23.821
I should do it more often, but whatever, it's what I do.
00:20:23.821 --> 00:20:26.963
And now I've got all these colors we already talked about.
00:20:26.963 --> 00:20:29.411
Purple has something to do with my podcast, right?
00:20:29.411 --> 00:20:31.303
Blue has something to do with my training.
00:20:31.303 --> 00:20:34.570
Black gray color is associated with my business.
00:20:34.570 --> 00:20:49.131
This orange stuff is, you know, relationships, people, industry committees, et cetera, and so I can come through here and I can just at a glance look at all the things that I have going on and I can see how frequently they're happening.
00:20:49.131 --> 00:20:51.909
Oh, I'm not even sharing the damn thing here we go my bad.
00:20:51.909 --> 00:21:01.711
So I can go through the Trello board here and I can see at like this is current as of right now, and I can look at all the colors and see where am I spending most of my time.
00:21:02.420 --> 00:21:05.640
Now there's some stuff here like this social marketing.
00:21:05.640 --> 00:21:09.689
That's like me posting and creating posts and commenting and all of that.
00:21:09.689 --> 00:21:14.267
That's coming up quite a bit and I know how much time it takes.
00:21:14.267 --> 00:21:24.290
If you're on here, you know how much time it takes, and so for me that might be a signal that I could do something about it or that I should maybe consider outsourcing it.
00:21:24.290 --> 00:21:25.250
I won't, because y'all know I love all the attention that I could do something about it or that I should maybe consider outsourcing it.
00:21:25.250 --> 00:21:28.972
I won't, because y'all know I love all the attention that I get from you guys and the interaction.
00:21:29.861 --> 00:21:32.866
But the point being is, when we track it right, create the tide.
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