228: The Burdensome B’s—Four Red Flags Signaling it’s Time to Make The Big (Delegation) Leap

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It doesn't matter if you can get by at doing them. That probably means you shouldn't be doing them at all. Because as the business owner, as the visionary, as the creator, the one with big ideas, some integrator stuff is okay. Some of the operational stuff is okay. But if you get bogged down, if you keep too much of that on your plate, your mind will be too cluttered too to do the big stuff. The things that you are truly unique at.

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I was having coffee the other day with a friend and fellow business owner, somebody who's been self employed for two decades now, if not more, and he showed me something that broke my heart a little bit. It was a message from one of his team members and I immediately felt so bummed for both of them because both were feeling frustration for something that didn't have to be that way. Today I'm going to share three red flags to look out for in your business, especially as it relates to delegation. Hint hint. And I'm sure there are hundreds more. So I don't have to tell any of you running your own delightfully tiny team and small business that flags abound, I would love to hear from you. As always, if you want to share any of your big ones that you look out for, smoke signals that something really needs to change, send them to me@hi time.com or submit a voice memo@itsfreetime.com Ask so what was it showing on that phone screen? It was a laundry list of grievances. Things that were going wrong, things that needed to be fixed, things that were overdue, things that this person was waiting on. These things are so normal they're going to happen in any business in any householding for that matter. The frustration came because this team member was waiting for things on the owner of the business's desk, both the physical desk and the physical space where they run the business. But also things that needed to possibly happen online could have been things like paying bills, submitting things for review. We all have this. We all probably have a paper pile literally sitting at our desk, and a proverbial pile of things that are piling up on our desk. That is the definition of a bottleneck in the business, where so many things are waiting for you, the owner, to approve or take the next step on that. It becomes a big pile and the work stops and slows down. This in turn creates a lot of friction for your team, who starts getting frustrated because they feel like their hands are tied, they can't make progress, they're waiting on you, and maybe you're overdue at getting back to them. This is the first Red Flag team member frustration. It's a sign that you're taking on too much. Things are piling up at your desk. You are the bottleneck, and especially for things that you don't even like doing in the first place. So you're both frustrated. You feel like you just can't keep up. There's never enough time, there's too much on your plate, and there's no way you can get to these smaller priority things. Meanwhile, your team member is frustrated. As we talked about, the second red flag is one I experienced just myself the other day is missing deadlines. That's a sign that you're over committing and likely over committing at something that you might not be very good at or maybe you should stop committing to in the first place. In my case, this example of a missed deadline, which always makes me cringe, but I do learn so much from these mortifying business moments, as I call them large and small. In my case, I had agreed to do a written Q and A. This is my Achilles heel. If you have been listening to this podcast at all for the last five years of the Pivot Podcast, previous to this one, I talk about how writing articles for publication is just not my jam. Yes, I'm writing more now that I have rolling in dough on Substack, but in general, answering questions in the written form. If it's not a podcast interview, it's just my Achilles heel. I procrastinate, I dread doing it, and I miss deadlines. So sure enough, I optimistically agreed to answer a few questions for a publication that sounded fancy and I was really, genuinely excited to participate in, but I forgot that I'm really bad at this, especially when I'm not making the core deadlines for my delightfully tiny media company in the first place. So, sure enough, the Friday deadline passed. The the weekend blew by. It was Monday, I still hadn't turned it in. And then the person's following up with me for a second or third time saying, hello, where is this? Are you still going to do it? This morning on my way into the podcast recording studio, I sent an email. I'm so sorry, sincere apologies. I wasn't feeling well over the weekend and that was true. And I kept waiting to feel better to get you the answers to these questions. But actually, as I reread the questions, I realized I'm not even equipped to answer these. They were about CEOs for bigger businesses and I felt like this wasn't even my zone of genius to answer questions like these. And we're going to talk about that phrase as it relates to one of my all time favorite books, which you probably already know, the one that I'm thinking of. I could have phoned it in, I could have plugged those questions into ChatGPT, judged it a little bit and tried to make it not sound like an AI answer. But I didn't. Instead, I owned it. I apologized, I missed the deadline, I hope it didn't impact his workflow too much. And I said to my team member, we've got to stop saying yes to these. It wasn't his fault, it was entirely mine. That was a signal that missed deadline that I had over committed and specifically at something I'm not good at in the first place. The third red flag relates to the first two is overwhelm or burnout more broadly, where you're actually starting to resent the work, even the work you say you love and or your clients, to where every ping, every email, every task starts to feel like an insult. Who needs me for what now? I'm getting so tired of this. And you start to feel the joy getting drained out of even the things that you like doing. In my case, I love podcasting. I love interviewing people, I love writing. But when I start to dread the fact that I have a podcast interview that day, or I feel underprepared heading into it because I'm overwhelmed and maybe I was feeling under the weather so I overslept so it cut into my prep time. There's this whole chain of events that can happen when you're doing too much, you're overwhelmed and you're burning out and you just need a break. In the introduction to Free Time, I ask are you beset by the burdensome bees? In the book, I share three, but I've since amended that to include four of them, many of which we've already just discussed. So the burdensome Bs are if you're feeling bottlenecked, burned out, buried by bureaucracy, or bored, four red Flags to signal that maybe you want to do things a little bit differently I'm really excited to give you a sneak peek at a permission slip from upcoming guest Andrew Davis. He says every time you say yes to do something new in your business, stop doing two things. What I love about this advice, this permission slip, is that it's really system thinking. Because in doing something new and stopping two things, you're proportionally and perpetually freeing up even more time. I've talked about this in the past that a lot of us business owners are visionaries to. Reference the book Traction by Gino Wickman and Rocket Fuel, the other one that he wrote. He talks about how a lot of businesses have a visionary, the one with all the ideas that's creative and big thinking, and they need some kind of support from an integrator role or a COO or a chief of staff, somebody who's going to keep the trains running on time. Now, in my business, I get a little bit torn because I have elements of the visionary, but I love doing the integrator work. That may be part of the reason that I like having a delightfully teeny tiny team, because I actually like doing some of the systems and structure and backend work. I enjoy that. I don't actually want to give it all away, but I need to give the majority of things away, especially the ones that I don't like doing and that I'm not very good at. That brings me to one of the books that changed my life when I first read it in 2009, and I've referenced it so many times since. That book, I hope you've read it too, is called the big Conquer your hidden fear and take life to the Next level by Gay Hendricks. Gay Hendricks is a longtime teacher of spiritual principles. He and his wife do a lot of work together. They have the Hendricks Institute. He has now a Big Leap podcast that I'll link to in the show notes. This is a small book and yet it has had such a big and profound impact on my life and even the way I think about my business. So for the unfamiliar a go out and get this book right now. Do not pass go. You can probably Read it in one sitting. Although there's a lot to really sit with and live with within yourself. But there's two things that I want to highlight as it relates to these flags that we're talking about in the business. The first, and he's now famous for this, is identifying the four zones of functioning. The zone of incompetence, the zone of competence, the zone of excellence, and the zone of genius. Now, a lot of what we're doing here in running our own delightfully tiny creative businesses is trying to eliminate a lot of the work that isn't our zone of genius. You've probably heard that before. That part is the quest that we're on. I often think of it. It's a bit cliche, but like Michelangelo carving away at the St. To get to the angel, inside that angel is our unique gifts. And we need to keep clearing away the clutter and the stuff that we're only marginally good at so we can get to what we are truly genius at. But where a lot of business owners get stuck is not even in their zone of excellence, but their zone of competence and incompetence. Those will drag you down. So incompetence, he says, you don't even understand it, nor are you good at it. In the zone of competence, you're good, you can get by, but you're not distinguished in any way. The zone of excellence is another big trap, because you're doing something you are pretty good at, that you've built a reputation on, that you have a lot of experience with, and it kind of lulls you to sleep a little bit. The zone of excellence are things that you kind of, yes, you get rewarded for, but they're not truly your zone of genius. The work that you and you only you can do, that state of flow, that inspiration where you feel incredibly lit up and alive and that you can actually far excel at compared to others in the category. So if you had to guess at what was on that laundry list of things that had been piling up for my business owner friend in the text from one of his team members, what was it? What category do you think they fell into? Pretty sure you could guess the answer. Not his zone of genius. The things that pile up on our plate, that cause frustration for ourselves and others are almost always in one of the three previous zones. Incompetence, competence, or excellence. It doesn't matter. If you can get by at doing them, that probably means you shouldn't be doing them at all. Because as the business owner, as the visionary, as the Creator, the one with big ideas. Some integrator stuff is okay, Some of the operational stuff is okay. But if you get bogged down, if you keep too much of that on your plate, your mind will be too cluttered to do the big stuff, the things that you are truly unique at. I would love for you, if you're listening to this right now, to do an audit. You can even write those four columns on a piece of paper at your desk. I'm a big fan of doing this observation analog style and really look at what percentage of your tasks on your to do list or your projects or even on your calendar fall into those four buckets. Where are you doing too much in your zone of competence or even incompetence simply because you haven't figured out an elegant way to say no to it? You haven't figured out how to delegate it to a team member. Or maybe you don't even have the team member yet that you would want to delegate it to. The problem is, if you hoard these kinds of tasks like they talk about so brilliantly in the book the One Minute Manager Meets the Monkey, monkeys represent problems, and if you keep all the monkeys on your desk, you're a veritable zookeeper. I talk about this in free time as well, and this concept became one of the most best selling HBR articles of all time. Because as managers and business owners, we tend to take the problems that people bring us and we keep them on our desk. Oh, okay, I'll get back to you with an answer. Sometimes it feels good to solve problems for people, but the better thing is to say you solved this. Let me know what you recommend and what action you will take by when if you don't hear back from me. So I've had to have conversations with my team with a podcast production company where I say episodes need to go live on schedule, with or without me. If I haven't written three key takeaways, which is part of our show notes, publish it anyway. I'll either add it in later, but I don't want to stop production because you're waiting on me. And for the first time, when I took a big leap myself to hire a production team instead of piecemealing together with different contractors where I still cognitively owned the life of an episode for the first time, we have been unfailingly consistent for two years now, and I produce 14 episodes a month. I don't know if I'll produce that much forever, but for now, the only reason that that is happening and happening so consistently is because I don't own the life of an episode. I had to explicitly say, you are to keep this going with or without me. Now the only way that they can do that is if I don't record something in the first place. But what this statement allowed me to do is focus on me being the one that figures out who I want to record with, who my guests are or what the solo topics are and record it. That's it. Preparing for the interviews. I have help from a team member editing them, reviewing that first pass of the audio edit. I don't even do that. I don't review the audio before it goes live. If I notice a problem with it after it has gone live, I'll say something to the team, which is very rare. But that way I'm not holding up any part of the process waiting on my review. I am willing to have things get published, even imperfectly, if it means keeping the trains running on time.

We'll be right back just after this.

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So if you have things start piling up at your desk, just consider could you flip the way that you ask your team to work with you to say, I need you to own things from start to finish in free time? There's a statement the owner is not the owner. And that came as a result of a mortifying business moment where one of my team members was waiting on me to confirm that a corporate client who had purchased a ton of Pivot workbooks that the funds had landed in my bank. But I was working on free time. I forgot to check after a week or two. Sometimes corporate funds take a while to land. The result of that was that the funds landed and we didn't thank the client or acknowledge the existence or send the workbooks or any next steps for a month. And I was so mortified to make it right. We ended up throwing in a keynote which was worth far more than what they paid for the workbooks. But still, this was absolutely mortifying. I had to say to my team member, and this is where I came up with the phrase, the owner is not the owner that you need to bug me. It's still your task. No task should be waiting on my desk. You bug me until you have what you need and we cross this thing over the finish line. But I don't want tasks punted to me to sit on my desk because I will surely drop the ball on them. There's no question. I just simply can't think about big ideas or write deeply personal essays while handling every single detail, large and small, for every client or community member, or even potential client and community member who's writing. And there is simply no way I can do that all. And I will only create frustration if any of my team members are waiting on me for too many things. The other thing that Gay Hendricks talks about in the Big Leap that has stuck with me ever since I first read it, is the upper limit problem. The upper limit problem is a way that we almost, and I would say even overtly, unconsciously hold ourselves back. We have a certain limit of how much success or happiness or love we think we deserve. And when we hit up against that upper limit, it's deeply uncomfortable. As it relates to this conversation, I also think we all have a delegation upper limit. We have a level of delegating that feels safe, that feels comfortable, that we've gotten used to. And then there's pushing past that where it's deeply uncomfortable, where we are nervous, we are relinquishing control, and we're trusting somebody else to not only help do the work, but own the process, to own the outcome of that work. And so if you feel yourself bumping up against a delegation upper limit, where, oh, I can't possibly delegate that, that's really where there's possibility to inquire. Because the risk, if you don't push past that delegation upper limit, the risk is you start to resent the work, you start to get bored, bottlenecked, buried by bureaucracy and burnt out. And nobody wants that. And then what's going to happen is the entire business is going to sputter to a stop or your team members will get so frustrated that they leave, or they feel unseen, unheard, unappreciated. And no matter how well intentioned you are, if you don't push past these delegation upper limits, you will just increasingly feel burdened and feel like running your business. It's no longer fun. And then more serious problems can occur downstream consequences of missing deadlines or not paying bills or any of the little nitty gritty things that need to get done, let alone in our personal lives. I really think that so many adulting tasks are deeply annoying and that the best systems thinking we also need to apply to the home front because we need to eat, we need to find time to exercise, we need to take care of bills and taxes and laundry. So many boring things that those of us running creative businesses would much rather be doing anything else. But the point is that if things are piling up and people around you, including you, are getting frustrated and overwhelmed, that's a red flag. And we all experience these. I don't think there is a way to exist to run a business or run a home where you don't encounter these red flags. The point is, there's nothing wrong. You haven't done anything wrong. But when you recognize them, say, aha, I must be over committing or keeping too much on my plate. What can I start saying no to? How do I get stricter about what I say yes to in the first place? And most importantly, how do I own this idea and communicate it to the team that the owner is not the owner? If things are piling up on my desk, I'm going to say something radical. That's not my fault. That's a systems problem because it means two things. The systems problem is that why does someone on your team think that the thing should wait on your desk? It's their job to own it problem, solve for it, keep bugging you about it. That's important. So nothing should just be languishing, ideally on your desk. And the other system's problem is that it's hovering in an indecision zone. Probably the reason it's on your desk is you haven't delegated it before, or you're not sure how to delegate it, or there's something important about it. Try to unpack that a little bit and figure out how can you ask for help at least with the next few steps? That might even be uncomfortable. Even if you can't delegate the entire thing, how do you keep this thing moving? For anything in that pile you can look for what you can automate, delegate or eliminate. Maybe some combination of those things. Is there any way to automate any part of this process? Can you automate when or how often your team members are Going to bug you about it. That's okay too. Some kind of a system so that it doesn't just stop and grind to a halt and wait in a pile, never to be seen again. Can you delegate any aspects like we've been talking about? Can you eliminate it altogether now? Let's say it's a tax bill. It just needs to be paid. Nothing gives me more dread than when I see a letter from the IRS coming in the mail. I absolutely can't stand it. And I'm always like, oh, what did I do wrong? Or am I getting audited? So of course, something like that. No, you cannot eliminate it. But let's go back to Andrew Davis permission slip. Are there things that are just no longer resonating? The life has gone out of them. You've neglected to do it now for nine or ten months in a row. Do you really need to do it or keep it on your plate for month 11 and 12? How much can you possibly eliminate? And for the really annoying stuff, I even have one friend who schedules a call with an assistant once a week. It's a three hour call and he just talks. It's almost like the business owner version of morning pages. He just talks freely for three hours and this assistant takes notes and summarizes them at the end of the call. Could AI handle this? Maybe. But it's important to my friend that he have a live person who's there listening and they have a scheduled call. It's like having a personal trainer at the gym. They have a scheduled call at the start of every week where he gets to just talk freeform. This isn't a meeting with a very clear agenda. 15 minute stand up. Nope. This is my friend's way to clear what's on his mind. Have somebody else present, observing, listening, note taking, who then spits the notes back so that my friend can then properly traffic direct all the tasks that might need to be done related to anything that was on his mind that week. The most important thing that these red flags highlight or the burdensome bees is that it's time to step back from working in the task so you can work on the process. This is something that I talked about in the conversation with Cal Newport. It's a big theme in Free time. The point is not to beat yourself up or feel guilty that you have this pile, virtual or physical, that's waiting at your desk. As the business owner, the important thing is not to just, you know, grind and then like rip the band aid and schedule a day and just power through it. The question is, how did this pile get here in the first place? How can I improve my systems or my communication or what I'm asking of the team so that the pile doesn't happen at all. So that things keep moving as quickly off my desk as they arrived. And again, if you want a real tiny kind of kick in the butt to do this, read the One Minute Manager Meets the Monkey. I'll put the link to that book in the show notes. You hereby have permission to stop doing things that you're not even good at. Drop them. Stop that. You're not even good at it. You're dreading it. It's draining you. You're procrastinating. Stop doing it. Figure out how you can get help from somebody on your team. It's okay if you don't even know who that team member is yet. Start designing a way so that you can stop doing it altogether now. Again, this may be as simple as shutting down a project, even a revenue stream. If it's something super annoying like bills or government business. I get it. None of us can drop that completely. But you hereby have permission to stop trying to be somebody you're not. If you are someone that hates handling administravia, you don't have to do it all by yourself. But you are responsible for helping create the system and the flow of communication that gets it back off your desk. So if you can do one thing next as a result of listening to this today, think about the one thing that you're currently the bottleneck on that drains you that you don't even like doing. And I just want you to ask, does it need to be done at all? And if so, what is the one next step that could help you delegate it to somebody other than you?

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