Episode 99: The Actual Doing of the Thing
How do you transition from being an “overthinker” to a “doer”?
Summary
This episode tackles the mindset gap between planning and executing in a solo or consulting business. Nick and Kai work through why overthinkers stay stuck and what it actually takes to ship consistently. Along the way they cover concrete tactics: impact/effort scoring, calendar blocking, and batching small tasks.
Highlights
- Nick spent the last five years moving from overthinker to doer. The shift required accepting that some work he ships will feel average, because you get known for what you create, not what you’re still planning.
- Kai distinguishes between anxiety about a task and genuine hatred for it. Anxiety is something to work through; hating the thing is a signal to stop doing it entirely.
- Nick uses the Jeff Bezos rule of acting on 70% of available information rather than waiting for certainty, and says it hasn’t backfired once.
- Naomi of Idibiz’s impact/effort scoring: list pending projects, rate each one to three on impact and one to three on effort, then focus on high-impact, low-effort items first.
- Kai keeps a running business development to-do list and works through it between bigger projects, especially when prospecting for new clients.
- Nick captures small tasks (under 15 minutes) into an OmniFocus context called ‘small win’ and batches them in scheduled blocks rather than acting on them as interruptions.
- If the next few weeks are already full, Nick’s advice is to book the thing you’ve been putting off one to two months out before the rest of that time fills in.
Read the transcript
This thing we talk about a lot on this podcast, where we talk about kind of the mindset shift necessary to really think like a business owner. And we talk around it without stabbing it dead. So we’re not gonna I don’t know if we’re gonna stab it dead. We’re gonna stab it a few times. And it might just go limping away bloody and miserable. Somebody asked the mind, this isn’t a question. The mindset change of transitioning from quote overthinker to quote doer. equals having a bias to take action instead of analysis paralysis.
I apparently added this to trello on October 18th and have no memory of that. So uh Don’t do drugs, kids.
Don’t do drugs, kids. Yeah. So, but there’s a sentiment in here about overthinking things versus executing. And I think that the biggest This is something we definitely haven’t talked about. The biggest thing that separates people who are successful at business from people who are not successful at business is people who are capable of executing. And people are capable of executing, are capable of planning, and not overthinking the stupid thing. And some of this involves taking on faith that what you are going to do is the right thing, right? And so there’s a lot of the more you spend measuring twice about an action, the less time you are spending actually doing that action. So there’s a point at which your worries about a thing cease to be helpful in terms of the planning phase, right? The other thing to be keeping in mind is that when you’re especially doing like a larger project, like a book or a course, or Like a radical re-envisioning of the way your business operates or something like that. There is always a next thing you can be doing. So the number one thing that I do is whenever I complete a task, I write down the next logical thing to be doing. And then I make I put that in my to-do, and that’s the next task I have for that particular project. And if you aren’t doing that, you’re going to forget. I’m at least absent-minded enough that I forget. Beyond that, the initiative to begin, I mean, that gets into a little bit of therapist territory, right? Like, nobody’s going to start the thing but you, right? We’ve talked about this on Skip Steps 1 and 3 before. And I think the sentiment there is very much the same, where you’re taking action and actually doing the thing.
I know that I, when I think back five to seven years, I was very much an overthinker. And the last five years have been transitioning to being more of a doer. And one of The key, one of the key points I had to accept was to be a doer, there’s going to be some amount of Dissatisfaction or feeling that it could be better, but around the work I produce. But I will become known for what I do and for what I ship and for what I put out into the world. So if I Get stuck overthinking and overanalyzing and over planning, but not doing, not creating, I’m not putting anything out into the world. So I needed to accept it’s okay and actually necessary to put things out that I feel are average or slightly below average and just get the things out there. Because once I get one thing done, I could move on to the next thing. And maybe today’s email sucked. Tomorrow’s is going to be better. Maybe this launch wasn’t as good as it could have been. Whatever. At least I was able to do the launch. Now I can move to the next thing. Accepting that completing a thing, as you put it, lets you identify the next thing you need to do. Well, once you complete it, you could get started on that next thing. And I think there’s a nice rhythm you need to get into there of saying, hey, I need to get this done so I could start working on the next thing. And when we ask that question, it brings to the surface topics like, okay, how could I get this done quicker or more efficiently? Or what outcome are we actually aiming for here internally to working on your business or working on a client project? Just understanding what outcome you’re aiming for, what would need to happen for you to be able to check that task or check that project off. That gives you so much more freedom and clarity because you can say, okay, I need to do one, two, and three. I’ve done one, two, and three. The thing is done. I know in the past, I’ve always suffered from overthinking it and saying, well, do I need a four, five, and six here? What if? What about this? What about that? But focusing on saying, okay, what’s the minimum necessary to complete this? Now I’m going to do it. Okay, it’s done. Now let me move on to the next thing has been liberating and let me tackle more projects and complete more things in a year than I previously was able to. Yeah.
So there’s kind of two things that happen when I’m feeling my own personal resistance to doing a thing, like even initiating it or continuing it. And one of them is that I’m anxious about it, in which case I need to get over my problems. and then sit down and journal and figure out exactly what it is that’s holding me back, and that’s like a me thing. The other possibility is that I actually genuinely hate doing the thing. In which case I shouldn’t do the thing. It’s making me miserable. If you hate repositioning your business again, don’t do it. But if you you can’t mistake hatred for the thing for like something that’s actually genuine. about your like anxiety around it, right? That’s like something that you need to personally resolve. 99% of the shit I do, I need to personally resolve. But I’m in a good position right now where I have decent clarity about what to be doing with my business. People are not lucky with that when they’re just starting out or something like that. So, yeah.
There’s that Jeff Bezos quote about making decisions when you only have 70% of the necessary information. And that’s been a guiding quote for me this year. I have multiple times said, I don’t feel 100% confident in this, but I feel 70% confident. Let’s just go with it. And it has yet to bite me in the tucus. It has been a valuable. Decision-making device to say, well, I might not have all the information, but I have 70% of it, and I feel like it’s a go. Let’s do it. I, I. Highly recommend that for anybody that feels sort of stuck or paralyzed. There’s also this Tumblr post I read years and years ago. But it’s stuck with me to this day. We’ll get a link into show notes, but the summary of it basically is: be more aggressive in your life. Pretend that you have a year and then you’re going to get a day job. You’re going to give up. You’re going to switch to a different industry. You’re going to change. You’re going back to school. But you have one year to be as pushy or as aggressive or as forward as you want or can be. Go and do it and see what happens. And what I’ve discovered is by following that as a directive, by having that as something that I live by. I naturally say, hey, what about doing this thing or taking this chance or trying this project? And it leads to more opportunities. I’m fond of saying that the best way to get a seat at the table is to show up with your own chair and to just sit down. And I think this idea of being more aggressive in our actions and making decisions with a little less information than we’re comfortable with plays directly into that. It makes it easier for us to say, hey, let’s try this thing. But I think the third thing that couples into it is becoming good at recognizing when you’re heading down the wrong path or making a mistake. You launch a new line of business but decide it isn’t right, or you pick a new positioning or target market, but then say, ooh, I don’t like working with this group. Great. Say, hey, I made a mistake. Let me backtrack. There’s no problem in saying, I tested a thing, I discovered I didn’t like it. I’m going to roll back and try something else. That’s how you test design. That’s how you should test anything in life. I think. By combining this intention with being more aggressive in what we try to do, acting more in our business, with an ability to recognize when we’re heading down the wrong path. It makes it easier to try new things, test new things, and get to a point where we know more about our business. Even if we try, say, a dozen things in a year and each one flops, well, At least we took 12 ideas that we were sitting on and overthinking and tried them and said, well, none of them worked. But at least we’re able to go from overthinking them to saying, these don’t work for this business. Let’s try something new.
Um I don’t get the people who seem to act as if they don’t have only one life. Because the instant you know that you’re gonna die And I know this is going to get real dark, but like the instant you know that you have one life, or maybe you believe in reincarnation, I don’t, when you know you’re going to die, that’s a big fucking motivator. That’s the real thing. And Steve Jobs even talked about this in his Stanford commencement speech, which he was wrong about a lot of things and then died. But he was right about this. And he acted he really walked the walk. He actually took action on it and lived as if there was urgency in his life. And if you aren’t doing that, you need to start. That’s the real thing. You need to live intentionally and carefully, or I mean, that’s a bigger motivator to get started with a project than anything else that I can think of.
It’s a bigger motivator, I think, to decide what projects to work on or what to focus on. You’re absolutely right. When you put it into the scope of you get one life, you have 30 to 60 years left on this planet. What you gonna do? It sets a fire under your tukkus in the right way. It motivates you to say, Hey, if I’m going to spend five to 10 years working on this thing, do I actually enjoy it? No. Okay, I’m going to jump and do something else. I know that when I left my day job employment to work as an independent business owner, there was a bit of that in there. I was saying to myself, Hey, do I really want to spend 40 years at this company to become a VP? And da da da? No, I do not. Boom. Made the decision so easy for me. I realized that. In my life, I didn’t want to look back and see this is a past. I wanted to have a different story. And so there’s been a lot of intentionality around trying new things, testing new things, moving towards. Something new and something interesting because you’re absolutely right. We get one life. Why not maximize the amount of happiness or adventure or joy and delight you get in that life through whatever means it means?
Are we just going to be cheerleading for the rest of this episode? Like, what else are we going to do? What else helps as far as tactics around this?
I’ve found it very useful, and this comes to me from Naomi of Idibiz. When I’m overthinking different projects I want to work on, let’s say I have like 10 different things I want to do and I can’t decide which one I want to work on next. Writing them down on a sheet of paper and just saying, Hey, on one to three, how much will this impact my business? One to three, how much effort will this take? And then looking at that and then seeing, okay, well, this will have a lot of impact on my business. Maybe it’s launching a new service offering that I know people want or repositioning my business to a target market I’ve been meaning to. And it’ll be low effort. Hey, I need to update a couple of pages or send an email or take the sales page live. Looking at these and seeing, well, how much effort will it actually take versus how much impact will it have on my business? Has often helped me cut through an overthinking phase and say, okay, yeah, I have 10 ideas here. Eight of them are pretty hard to do and won’t actually make the boat go faster. These two, they seem pretty easy and they’ll make the boat go faster. I should focus on those. So that’s been a, I guess, a habit of analyzing the different options in front of me and stop overthinking and just isolate down to what I want to focus on.
Another thing that I do, I actually keep a business development to-do list. And so, whenever I’m bored, which happens I just start knocking it out. And that’s like, it’s all of the deck chair moves and all of the like actual interesting things that I could possibly be doing in my writing practice. And my outreach practice. I tend to knock through that very quickly when I need a new client.
Yeah. Yeah. I have a this is something I started doing this year, and it’s been really valuable. I use OmniFocus for task management and I have a contact set. Small win. And it’s just something small that’ll take under 15 minutes to do. But it’s where all those tiny wins like update the sales page to include a reference to this, answer this question in the email sequence, fix this bug on the site. Raise the price on this, end up going. And when I set out a block of time and just start moving through them, I know these are tiny things that feel like interruptions that they come up one and two during the day. But if I sit down and break through five or ten of them and do that consistently week after week, I’m going to be making massive movement forward in my business, fixing the bugs, fixing the issues, making it a smoother experience. Addressing actual customer feedback or questions and complaints, and building a better, stronger business. So, focusing in on those small wins and giving myself time to actually execute on them instead of using them as distractions as they popped up. I just capture them, get them into omni-focus, and say, well, this isn’t something that I need to fix today. It’s something I need to fix in the next month. I know I have time on my calendar to tackle these types of tasks. Great, I captured it. Now I don’t need to think about it until it’s time to work on those types of activities.
Yeah, and stuff gets on there pretty often. Like it’s easy to add things to the business development to-do, and it’s kind of hard to knock them off. It’s very easy to ignore that list. I would caution against doing that. And then that’s like the miscellany side of things, which is kind of the like one-off stuff. And then there’s the like Big projects and like planning it all out. And it’s so easy to get into the meta conversation of how to actually execute on something But like actually doing the work is how you’re going to promote yourself. And if you don’t have the confidence to do that, like you’re not going to put out new work. It’s going to be hard.
Yeah. Yeah. Now, you get known for doing what you do. You get known for what you ship and what you create. And if you’re constantly overthinking it, you aren’t going to be creating things. It’s a common piece of advice that I give on Make Money Online and give to people on my mailing list and my coaching students, but I’ll say it again here. It’s easiest to do a thing if you block the timeout on your calendar. Even if your next two to three weeks are just completely slammed and you’re like, hi, I can’t put anything on my calendar. I’m book solid, go out a month, go out two months. That thing that you’ve been overthinking. Schedule it the first availability you have one month out. And so, when you start filling in that month, you already have four or eight hours blocked out to do that thing, or maybe only one or two hours, but you’ve already scheduled it. Now you could schedule around it.
Yeah, and also like the idea of being quote booked solid is a fake idea. It really is. You could be booked solid, but like you’ll make time for something if you actually care about it. You choose to do the things that you do. That’s it. You will make time if it matters to you.
Yeah, I completely agree.