How to Organize Your Digital Life & Reclaim Your Time with Shawn Lemon – EP 219

Interview with Shawn Lemon

How to Organize Your Digital Life & Reclaim Your Time with Shawn Lemon

What if you could reclaim hours of your day just by getting digitally organized? In this episode, I’m talking with Shawn Lemon, Founder of The Digital Organizer, to uncover the systems and strategies that help entrepreneurs, executives, and busy professionals regain control of their digital lives.

From simplifying email management and file organization to choosing the right project management tools, Shawn reveals how a streamlined digital workspace can lead to less stress, more productivity, and a better quality of life. He shares insights from his time at Apple, lessons learned from working with top-tier clients (including his father-in-law, Michael Hyatt), and his approach to building systems that are easy to manage and scale.

Whether you’re drowning in emails, struggling to manage passwords, or just tired of wasting time searching for files, this episode is packed with actionable tips and resources to help you create order from chaos.

In this episode, you’ll learn:

✅ The exact tools Shawn recommends for email, password, and project management—and why some popular options should be avoided.

✅ How to eliminate the headache of juggling files across platforms like iCloud, Dropbox, and Google Drive by consolidating everything into one organized system—saving you time and stress.

✅ How a streamlined digital workspace can free up your time, reduce stress, and improve your productivity.

Featured on This Episode: Shawn Lemon

✅ What he does: Shawn Lemon is the Founder of The Digital Organizer, a company dedicated to helping individuals and teams simplify their digital lives. He specializes in email, file, and project management organization, and he’s worked with clients like Michael Hyatt to streamline their workflows and improve productivity.

💬 Words of wisdom: “Fighting with technology every day is just not a good feeling. So, we come in, consolidate, organize, and teach you how to operate digitally in such a simple way that makes it so that you can find what you’re looking for in seconds.” – Shawn Lemon

🔎 Where to find Guest Name: Website | LinkedIn | Facebook | Instagram | YouTube

Key Takeaways with Shawn Lemon

  • Intro to Shawn Lemon
  • What is The Digital Organizer?
  • Creating a reliable organizational system
  • Shawn’s hybrid approach to email management
  • Why most attempts at outsourcing email fail
  • Password management best practices
  • Project management tools: Asana, ClickUp, and Hive explained
  • Cloud storage solutions: Dropbox vs. Google Drive
  • How to work with The Digital Organizer to build your system

A Solution to the 2-Step Verification Headache

Inspiring Quotes

“Fighting with technology every day is just not a good feeling. So, we come in, consolidate, organize, and teach you how to operate digitally in such a simple way that makes it so that you can find what you’re looking for in seconds.” – Shawn Lemon

Resources

Tax Strategy Masterclass

If you’re interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax

Strategy Session 

For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation

The Lifestyle Investor Insider

Join The Lifestyle Investor Insider, our brand new AI – curated newsletter – FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider

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Read the Full Transcript with Shawn Lemon

Justin Donald: What’s up, Shawn? How are you?

Shawn Lemon: Doing well. How are you?

Justin Donald: Doing great. Good to have you on the show. And I’ve heard a lot about you now. We have some mutual friends and namely, your father-in-law, Michael Hyatt is a good friend and someone I coached with for, really, what, the last year? I think I just wrapped up my first coaching agreement with him, like, I don’t know, last week or the week before.

Shawn Lemon: Yeah, that’s awesome. Well, I love him and everything that he’s doing and their business over there, it’s been a joy. I actually did their tech support and helped kind of build out their whole systems and everything from Platform University launch all the way up until right about when my son was born. And so, I made some transitions to do focus more on digital organization. And yeah, I love Full Focus.

Justin Donald: Well, how on earth did he not wrap you in long term? So, I’m wondering like, how did you go in a different direction where you have your own business and he didn’t talk? I mean, he’s a good sales guy. So, how did he not talk you into Full Focus?

Shawn Lemon: Well, I’ve always just wanted to kind of do my own thing. It was kind of tempting at times, but I started this whole thing just wanting to learn how to start a business and be successful at it. And, yeah, just kind of figure out how it all works, but yeah.

Justin Donald: Well, I am glad that you went with your gut and started the business that you started. But I think the world of Michael and I just think that he’s brilliant and he’s fun and he’s unlocked a lot of cool things that we’ve been able to utilize in Lifestyle Investor. So, for us, like, even though Michael is expensive, it was well worth it because, and for those that want to hear more and hear the episode, check it out. It’s probably months ago at this point. I did an episode with Michael Hyatt.

But even charging $150,000 a year, whatever it was, we made way more than that just on one single idea that he gave us. And it pays for itself many times over. And so, it’s always an interesting thing with pricing where the price, I always tell people the price is irrelevant, and people who think more linearly, they’re like, no, that can’t be true. It’s X amount of dollars and that’s a lot of money. But I have to remind them, whatever the X per dollar is, if it’s $100, $1,000, or in this case, $150,000, is that number really that relevant if you made $1 million as a return on that investment in yourself and in your education? And which, for us, it was not too far off that number.

Shawn Lemon: Yeah. What’s the return? It’s amazing how often we can get caught up in that sort of thing. I see it all the time with what we do. I had one guy, I was showing him a $300,000 upside on an $8,000 investment and ended up getting crickets because I don’t even know why. It was the oddest thing. And sometimes you just see it and say, “Oh, I don’t know.” It, yeah, kind of boggles my mind when it’s just about return and then lifestyle as well of how much better your life can be.

Justin Donald: That’s right. Well, and that’s really what you do, you spend a lot of time. So, I mean I’d love to hear about your time with Apple prior to, but before we do that, tell me as succinctly as you can what your business is about, The Digital Organizer. Help me understand exactly, well, I kind of know, but just to help our audience understand exactly what you do.

Shawn Lemon: Yeah. So, the chaos of not being able to find what you’re looking for, from your files, your email, understanding what you’re supposed to be working on, what your team is doing, and being all aligned with project management, where you find your files, how you’re communicating with each other and, of course, passwords, which is just a daily thing, that’s what we do is come in and overhaul that. So, we’ve got the typical client comes to us because they’re having a really hard time finding what they’re looking for. A lot of times, multiple versions, their email is just exploding and they’re not sure what they’re supposed to be working on every day.

And if you’re trying to scale or you’re just trying to be productive in your normal life because you’ve got a lot of investments, got a bunch of things going on, fighting with technology every day is just not a good feeling, how we spend our days, how we spend our lives. So, we come in, consolidate, organize, and teach you how to operate digitally in just such a simple way that makes it so that you can find what you’re looking for in seconds.

Justin Donald: Yeah, today’s world, you really need to be digitally organized. And by the way, some of that infrastructure can be people, but it needs to be built at some point in time. So, anyone that gets plugged in has the ability to access what they need to access, right?

Shawn Lemon: That’s right.

Justin Donald: It’s got to be more systematic than, like, oh, I give this example all the time because sometimes my office can be a little bit of chaos where it’s like, I got these books here and I’ve got these papers and it looks like disarray, but in my head, I’m like, well, actually, I’m not moving that because I have not completed the item on this or it’s sitting on my desk and I’ve got a pile over here. And these books like this, I’ve got an article in this book or an excerpt that I need to work through and unpack.

And so, like, I have a method to the madness, even though it doesn’t look nice, but I think, my wife is the opposite. Her workspace is pristine and she knocks out everything she needs to. By the end of the day, she wraps up nice and neatly and I wrap up very, maybe chaotically because I’m working more on a longer term. But I think any way you look at it that there needs to be some sort of organizational system. Mine could be cleaner, but I do have a system.

Shawn Lemon: Yeah. That’s the most important thing is just having a system that you can rely on. And David Allen talks about this in his book, Getting things Done, and the courses and stuff that they sell. But the main reason why we want to leave something on the desk or leave something in the inbox is because we don’t have a system that we can trust that our unconscious can let go of and say, I know that that’s in a place that I’m going to check it later.

But the problem is some people still have a hard time doing routine work. I’m one of those people of, like, I want the next thing, I want the next problem to solve, not to sit down and clear out my inbox and do administrative work. I do it because I have to, but I’m trying to minimize that as much as possible by changing settings, making sure that I have places digitally to save everything so that when I get it, I can do it immediately, put it in the right spot, know that it’s named appropriately, or it’s going to be on my calendar. It’s going to pop up on the right day and time, so that I can truly let it go. Otherwise, things get piled up so much, especially when we’re busy and we have a lot to do.

Justin Donald: So, I’ve got to imagine you get this question a lot. Doesn’t just having like an email organization system and there are a bunch of them out there, if you have executive assistants and virtual assistants using something like Missive, if you’re maybe more of like a one-man or one-woman team, maybe Superhuman. And there’s a number of these companies out there, and I’m sure that you’re going to say, “Hey, these are good. It’s better than not having them.” But does your system include some sort of email organizer? Or is your system, like, does it help create that email organization?

Shawn Lemon: It’s a little bit of both. So, typically, we’ve got the programs that we like best, like, Missive is one of the tools that we often recommend, SaneBox, sometimes Superhuman. It really depends on the person’s needs and what their inclinations are and how they work as a team or not.

But the main thing is most people’s inbox is overflowing by junk. So, we have to clear out all of the stuff that’s overwhelming the inbox in the first place. So, we’ve got to make sure that we are only getting email that we truly want. And then from there, creating a triaging system that actually has to do with calendar, when are we going to make time to deal with the different types of requests that we get? And then from there, we can utilize tools and apps, like Missive, Superhuman, whatever, to be able to schedule things at different times, to be able to share them with an executive assistant that we’re working with, or they’re the ones actually checking the email and they share it with you when there’s something that they can’t handle, which is even a better case scenario.

So, it’s a hybrid of all of that. We want to get the email account under control. We want to make sure that we’re using the right tools for that scenario. And then we need to figure out a triaging thing with the calendar of when is the best time to do this type of thing. So, we’re just not a slave to email and we’re doing things when it makes sense to us and we’re just not bouncing from task to task all day.

Justin Donald: Well, I’m such a big fan of buying your time back. I talk about it all the time. And part of that is, from the standpoint globally, if you buy assets that produce income, then you’re going to buy back your time, right? Eventually, you’re going to have passive income that covers your lifestyle expenses and then you don’t have to work. You get to work.

On a smaller scale, though, you can buy your time back via people and roles, people you would hire and plug in to play to do different things. I do that with a CFO. We have a family CFO. We’ve got COOs or operators in each of our businesses. I have virtual assistants, executive assistants. And so, all these things really buy time back. And I love that.

But then there are systems that exist that buy your time back. And then there’s technology that can help buy your time back. And I think that we should be playing in all of these arenas to be able to truly own our time and not be caught in the weeds, doing things that don’t justify our knowledge and expertise and use of our time. And I’m curious, if you can unpack, like what your system is or what are all the things that The Digital Organizer touches on, so people can, I guess, make some sort of a judgment on whether this is a product they would need and use?

Shawn Lemon: Yeah, totally. So, we’ve talked a lot about email already. But listen, I’ve been a little bit more into that and that a lot of times, we’ll have people wanting to offload their email to an executive assistant, but it doesn’t end up working out well for them because that person is basically just deleting emails, reading, trying to respond as best they can. But a lot of the emails that take up the most time still get dumped right on to the plate of the person who’s hiring that person to take care of it for them.

And so, people are usually trying to find people as the system and put a person and say, you create that system for me. But most of the time, unless you find just a real outstanding A player, they are creating a system for themselves and then they’re just trying to manage you as best as they can. I’ve got a good example of Hillary, who she’s an attorney. She’s got an extremely successful law office in Arizona and tons of stuff going on. She hates email, blown through so many executive assistants.

And she finally came to us, actually, by Michael’s recommendation. She’s in one of his masterminds. And we went through to figure out what’s the system. Let’s work together to create this system so that you never have to go in email again. And now, all she does is she works in Microsoft Teams, and someone else checks the email and forwards it to this channel that she can respond to, so she never has to check an email.

So, it’s things like that of will clear things out and make sure that you get way less email and then work creatively to figure out a solution where it is going to take a little bit of your time because we have to make it work for you so that the people, the cheap people who are doing this can be interchangeable. So, a little bit more investment on the front end, and then you really set up for success. Someone leaves you, just slot someone else right in and teach them that system or set them up with a session with us, and we’ll update them on how that works. So, that’s one of those.

Another would be files organization. So, a lot of times, we’ve got iCloud, Dropbox, OneDrive, Google Drive. We got a bunch of these different accounts or stuff spread out all over the place. Let’s consolidate all of it together, so you’ve got one source of truth and teach you how to operate in the cloud so that you’ve got project management. You have our different ways that we communicate and we still only have one place that we store our stuff and how do we do it so that when we get communication, that turns out to be a task, but if it also has an asset, we know exactly where that stuff goes, so that there’s a place for everything and all of them are working together.

So, files organization, password management systems, we solve all the two-step verification issues. And then project management, how do you know what you’re supposed to be working on a day? You’ve got a process that you always do over and over again for your investment properties or for something that you do in your business, let’s template that out so that you do it consistently and someone else can take that off of your plate so that it’s an SOP and it’s a checklist all built in one that you can actually see and check in on if you want to do that.

Justin Donald: And so, on the password management, I’m assuming you need a password manager in today’s day and age, like, I can’t understand how anyone operates without one. I mean, that was a game changer. And then, for people unfamiliar, there are ways that you can give access to people on your team, to people on your staff. They can authenticate so that you don’t always have to be authenticating and then they have permissions on what they can and can’t access, which I think is incredible.

I mean, we’ve just, and by the way, a lot of these password managers have gotten hacked over the years. So, there’s really only like a small handful that I think are like the trusted sources these days. I’m curious who you guys recommend or you choose not to recommend.

Shawn Lemon: Yeah, we use 1Password and recommend that exclusively. So, often, we’re trying to pull people off of LastPass with how many times that they’ve been hacked.

Justin Donald: I used to be on LastPass, I had to move.

Shawn Lemon: Yeah, totally. And some people are like, “Well, they’ve gone through all of this so that they’re going to be the most secure on the other side.” I’m like, “Dude, this the third time.” And the last time was so bad. Even still, I’ve known and loved 1Password for probably 15 years and it is just so good, both on Windows and on Mac.

And the cool thing is if you’re listening, if you have a team working for you, and especially for things like social media where you absolutely need two-step verification, I can tell you some real horror stories. That means it’s going to be really hard for someone else to manage those accounts for you unless you have a system in place, in which case you can have this app that stores your passwords, create a subset for social media or for finance. Like, my bookkeeper, I share a finance folder with them. And so, my tax stuff, everything has two-step verification and they have the codes and they’ve got it all and they never have to contact me to file my state taxes and franchise and excise tax, it all just gets done.

Justin Donald: Yeah. And one thing I will say, for anyone that’s trusting the outsourcing of financial information, please do not give access to your bank account info. Create another account, give permissions, like that is so, so important because anyone can have a bad day. And by the way, they could be the most honest people out there, but they could get hacked. They’re not going to be as delicate with the passwords and storage and all that as you are.

Shawn Lemon: And that’s another reason why to use something like 1Password. So, my key bookkeeper uses 1Password as well. But I tell you, if you don’t have every piece of information for that account, there’s no way you’re getting in. You have to know the sign-in URL. In the first place, there’s a unique URL just for you. And then your username, the master password, and then a secret key, and you can add another verification step on top of that. It is extremely difficult to get into that. Even as an admin to take over someone else’s accounts, you’re jumping through a lot of hoops.

Justin Donald: Yeah, I like that. Now, we did our research on password managers, and 1Password came into our final two and we ended up going with Keeper. I’m not sure if you’re familiar with Keeper.

Shawn Lemon: I am, yeah.

Justin Donald: That one actually won out in our assessment, barely. The two were basically neck and neck. But I’m curious why you like 1Password over Keeper.

Shawn Lemon: Well, it was around before. And then Keeper has made some really great developments over probably the past five years or so, that’s a real ballpark, that I’ve been paying more attention to them. But at first, it was pretty lame and didn’t have near what we had with 1Password. And 1Password has just always been at the forefront in my eyes from both functionality and design. It’s just, yeah, the way it worked and integrated with everything was just so good that we just went all in on them.

So, if someone’s using Keeper, great. Like, if you want to switch to 1Password, cool, but we can give you some tips to keep going with that. But it’s not that I’m not into them, it’s just I’ve made my bed.

Justin Donald: Yeah. Well, once you’re all in on something, it’s hard to pivot. But for those of you that are all in on LastPass or one of these other ones that has been hacked, there are easy ways that you can export your data. So, it’s not a manual effort on every single one of these. Okay, so what else? What are the other ways that we need to be thinking about our digital organization? So, we’ve talked files, we’ve talked password manager, we’ve talked email. Is there anything else that we need to be considering?

Shawn Lemon: I mean, really, it’s project management. And this is the area that so many people get caught up in shiny object syndrome, in chasing the next app because it doesn’t have the feature that they want or it’s not pretty enough. Or for some reason, that didn’t really work for them and someone else told them that they should use Notion instead. And so, people kind of jump from app to app when really, guys, the most important thing is figuring out what works for you and trying to get started on the right foot and then consistently using that one tool.

So, when it comes to project managers, they all do basically the same thing. And then it’s tweaking some settings here and there. I would do some research on the front end to say, what are you most drawn to that at this moment in time, the features and the design really pulls you in and stick to that? Download and hand pullover, whatever you need to do to get all the information out of the other platforms that you’re using, shut down those accounts and fully commit to one.

And if you need something else, you can use paper as an anchor as well, but it’s all about project management because we are getting spread out. Our to-do lists are massive and they’re all over the place. We have to-do lists in our Facebook feed, in our emails, in Slack, in Microsoft Teams, in our project management tools. The lists just keep going on and on. We have to pick one. And so, figuring out how to do that, finding the right platform for you, setting that up, and making it work for your team is something that allows teams to feel so much more focused and then just throw fuel on the fire if you really want to take off and get way more productive and scale or do something else or just have your sanity back.

Justin Donald: Yeah. So, I’m curious now which company is your favorite project management software. We’ve tried a few and we’ve got our one and two that we ended up going with. But how did those rank for you?

Shawn Lemon: So, Asana and ClickUp are two main ones, but we’ve recently just added Hive and we’ve got Annie, who’s our project management guru. She’s an Asana girl first. And then she got into ClickUp and it makes sense for a lot of people, maybe not for everyone, we tend to lean more towards Asana. But a few weeks ago, she emailed me about Hive. And so, like, let’s add that to the list because I’ve gotten into it and I’m obsessed with it. So, she’s really into it. We’ll look into potentially switching over. I’ve got so much integrations and stuff set up. Like, for me, a platform change is something that I am extremely cautious about, but mostly are really good one.

Justin Donald: You got to be serious. You got to be 100% to make that pivot.

Shawn Lemon: Yes. Yeah, you’ve got to be 100%, or use it.

Justin Donald: Their methodology and functionality is just a lot different.

Shawn Lemon: Yeah, yeah. What about you?

Justin Donald: So, we’ve recently heard a lot about Hive. But we kind of made our decision before Hive was anything big. So, we’ve heard great things. We came down to ClickUp and monday. And ClickUp was our head and shoulders winner. And we have been using that and have been very pleased and think that the functionality on ClickUp is more robust than any of the other platforms that we looked at.

Shawn Lemon: Yeah. And for the listeners, so with some of these different platforms, ClickUp is a really big, popular one out right now, especially because they’ve got so much functionality. They’re acquiring a lot of other businesses, they’re growing really fast, and they’re trying to be the one app that rules them all sort of scenario, which is really appealing for a lot of people.

I think there’s some danger in that, and using things like ClickUp, Docs, and Sheets, like, how are you going to get them out? I’m currently in the middle of a data migration for business, has got terabyte and a half worth of data, 8,400 box notes and box, if you want to leave them, you can’t get your notes out of that. So, the person who found me because we wrote an article about it and talking about the method of doing it by hand was 8,400 notes. There’s one company that has figured out how to do it.

Justin Donald: Someone’s got to write software extraction.

Shawn Lemon: I know, I know. Well, one company does it and they charge me $2,800 to do the migration. So, I’m actually working with them today on the whole thing and working it over when I’m paying $200 for the license for another competing product. And I’ve done 4-terabyte transfers for that in days. So, it’s crazy how, if you go deep into a platform that has just been designed to be very sticky so that you can’t leave, that puts you in an awkward position.

However, ClickUp gives you so much flexibility to create systems and your project management in a way that you can design it out yourself, whereas something like Asana, it’s on rails, man. You got your teams, your projects, your tasks and broken up in sections. And so, it’s very easy to use and intuitively structured. So, do you like a structured approach? Or do you know what you want? Have you figured out your systems and you want to be able to customize something exactly how you want to operate? And that’s where something like ClickUp comes in.

Justin Donald: Yeah. And I think for ClickUp, we like that we could add PDFs and we could add videos. And there was just, again, it was very robust. So, while we’re on the topic of bests and favorites, cloud storage, what do you think for that?

Shawn Lemon: Okay. So, we use Google Drive and we are 100% in on Google Drive. It’s our favorite. We’re platform agnostic when we’re working with other people, but we use Google Drive and often migrate people into that platform. However, I think the best one is Dropbox. So, as far as like a tool to be able to sync the files from your computer up to the server and one of your teammates has a huge file and it gets synced up, and that speed and accuracy of syncing across everyone’s devices, Dropbox has got it nailed. They were the first ones to do it and they have been on top the entire time. And their focus isn’t split like Google is and Microsoft and all the others.

So, I think SharePoint is a fantastic product as well if you’re in the Windows environment. If you’re mixed in Mac, then you might want to look elsewhere. But as far as sync tools go, Dropbox is the best. I love their interface too. For an admin, if somebody deletes something and you need to restore a massive folder, you can see exactly who did it when and restore it. It’s really nice.

Justin Donald: Yeah, Dropbox is for sure the industry leader. What I will say, there’s convenience if you are using Google for other things. If you’re using Gmail, if you’re using Sheets and just Docs and all that, there’s a beauty and kind of having one home for everything. But the thing I don’t like in the language of their agreement is that they actually say that anything that’s on their cloud platform, they own, like they have the rights to. Now, I don’t think they’ll actually end up doing anything with people’s content, but I don’t like the language. It is a little bit scary from a protection standpoint. So, that’s probably just me being a little nit-picky, but when I read that, I didn’t care for it.

Shawn Lemon: I don’t love a lot of Google’s practices, and yet, I’m there anyway because of convenience, because the tools are just so good. I’ve never had a corrupt Google Doc. I can’t tell you how many corrupt documents or Excel spreadsheets or PowerPoints that I’ve experienced myself. And then clients have come to me, these horror stories with, it’s like even the habitual commands as it’s just savers all day, but they don’t close the document and then the file still corrupts. I never have to deal with that.

And when I’m collaborating with someone else, I hire a lot of people in other countries to outsource work to, and the majority of them do not have Macs. But everybody’s got a Google account and as long as I’m using the right subscription and I set up the system, the right types of folders when I share with someone else and they put something in my folder, I own everything. Well, maybe Google, maybe I co-own with Google, it’s like saying I own my house.

Justin Donald: That’s the truth there.

Shawn Lemon: It’s also financed.

Justin Donald: Yep. Well, while we’re on the topic, by the way, side note, I love having my list of things. So, I kind of have like, a top three, top five, top ten list for everything. And I love kind of like creating my definitive list. So, while we’re at it, you mentioned a comment. You had said something about Microsoft Teams. And I’ve got to tell you, I think that’s the worst ranked video platform out there. So, I’m just throwing that out there. Now, I’m really curious who you like for your video communications.

Shawn Lemon: For video?

Justin Donald: Yeah.

Shawn Lemon: Zoom.

Justin Donald: Some people are forced into it because they are captive Microsoft customers, or their company uses it, but it is the least functional of all of them.

Shawn Lemon: I hate Teams and the fact that, like, you create a new team, then you want to upload it, creates a SharePoint attached to it, and then you delete that team and it deletes all the files that are in that SharePoint, it is just an organizational mess. And we’re talking with another, it’s a big managed service provider here in the Nashville area about trying to come up with a whole organizational system to take their clients through to say, okay, let’s figure out how to marry the communications and the file storage so that, because Microsoft is doing this, we’ve got to figure it out.

But the question was, what’s my favorite? So, Zoom for sure, number one, because it’s just so easy. I mean, I was on a Google Meet earlier. The quality is getting better, stuff is getting better, but the thing is, it’s just weird, especially if you got multiple cameras and microphones and stuff like that, that so many people have issues with it. So, it’s kind of a scary platform to work off of. And then you got Cisco and ends up doing the same thing and all the rest. I guess it would probably be Zoom first and then Google Meet after that and then basically whatever else I know.

Justin Donald: That’s right. Okay, we’re totally in agreement there. And in fact, it’s great because you and I are on the same page on all this stuff, which is awesome. So, I feel good. I feel confident now as a consumer, as a customer, a client of all these different companies. But I mean, I feel good about the research that we did because we take this seriously. If we’re going to use it, we want to use best in class products. And some people might be like, “Hey, Shawn’s giving away a secret sauce, but not really.” His secret sauce is the integration of all of them.

Shawn Lemon: It’s how you organize.

Justin Donald: Systems, how to use it, yes.

Shawn Lemon: Yeah, you can YouTube this stuff all day long and go to the University of YouTube and other blog articles to figure out this stuff. And if you’re good at figuring that out, great, you don’t need me. But the fact is a lot of people either don’t have the time or the technical interest to figure this out. In the end, we want to make sure that we’re on the right tool, but the most important part is how are you using it because there’s a lot of serious do’s and don’ts so you can’t get yourself into trouble over.

And architecting that stuff out at the beginning and just having that baseline understanding of the tools really sets you up for success. So, you can switch, you’re done with ClickUp and you want to switch over to Hive, cool. You know everything that you need and how to export it out. And you’ve got the good best practices where you’re uploading the PDFs and the videos or whatever into ClickUp. But you know that that’s all material that expires and we have copies elsewhere, so we can leave it and delete it and it’s fine.

So, it’s knowing how to use your tools that you can have the confidence to switch when it makes sense or to just settle in and say, you know what? Maybe someone else has got a feature that would make this a little bit easier. But the amount of effort in retraining across the board that it would take doesn’t make sense. So, we’re going to do this thing manually and it’s going to take us two more clicks, where it would have been no clicks somewhere else.

Justin Donald: Yeah, well, there’s a beauty for a lot of entrepreneurs that are hard charging, that are big vision, that are trying to change the world. There’s a beauty in just hitting an easy button and handing it off which I’m a huge fan of. And it’s interesting, like I’m thinking about all this stuff that we’re talking about here, and one of the best moves we ever made was hiring a good buddy to be the CTO for Lifestyle Investor because he’s helped integrate so much of the staff.

But someone could hire you guys for a fraction of the price, which is a great way to consider doing it, especially if you don’t have the needs full time to have someone in that role or even part time. We’ve done a fractional CTO and for us, that has been a good fit for a period of time, right? But I’m curious, tell us a little bit more about what working with you would look like.

Shawn Lemon: Yeah. So, usually, it always starts with a call to just see if we’re aligned and what you need. And if not, I point you in the right direction. But if you decide we’re a good fit, typically, what we do is we work with our clients to take them through a process, and we’re looking for somebody who knows where the bodies are buried in the system, but really understands the business so that we can work together to take you through our process of getting organized in the fastest way possible and then using the principles and all of the systems that we know and have learned over the years and figuring out which ones would be best.

So, we’re really co-creating an organization system together while we’re organizing and pulling files together and things like that. And then in some cases, there’s some real technical stuff. We’re doing a rebrand or we’re migrating from one system to another. We’re just going to get in there and do that for you because that’s not something that you really would be a good investment of your time to learn, but yes...

Justin Donald: Especially for a one-time activity.

Shawn Lemon: Exactly.

Justin Donald: There’s just not a lot of value in learning that, in my opinion. But I think it’s great for entrepreneurs to have an easy button. And by the way, not even exclusively to entrepreneurs, you can be a hard-charging corporate executive or attorney or whatever, and you just don’t have the time to do all this, but you need to get your house in order. That’s why I love them, all this company. I think this is brilliant and it’s a huge need out there. Now, I am curious how, you spent seven years as a creative at Apple, I’m curious how that time there helped influence what you’re doing today.

Shawn Lemon: Well, I mean, it was the whole impetus for doing it in the first place because I would have these people. So, I was a creative which means when you bought a new Mac, you’re offered a one-time opportunity to spend 100 bucks to get a year membership to meet with a creative and have hourlong sessions for us to teach you how to use your Apple products. So, amazing deal. And so, I would sit down with people for seven years teaching them how to do this stuff.

And they would get this new computer, take it to the store, well, their old computer and their new computer, the Genius Bar would transfer the data and then they would sit down with me to teach them how to use it. And they were expecting this fresh start. And then they’d get buried with all of the stuff that just got transferred over.

And there were so many people who felt really overwhelmed and had a hard time learning anything when the mess was there. And I just saw that over and over again that people were kind of frozen until they got control of the mess. Nothing could progress without it. Now, a lot of CEOs have a hard time understanding that because they can just pull right through and get things done. And it’s like organization, whatever, which just got to get revenue, let’s get it done.

So, a lot of times, it will have an operations person like, hey, I need help. And they’re like, just figure it out. So, that’s what I saw over and over again. And people started hiring me to come out and do it because the Apple Store didn’t do it. So, I would fill that need outside of the store and just helping out because yeah, it’s about, the Apple store wanted to teach you how to use something and I wanted to teach people how to figure out what they want to do in the first place and then learn that because there’s so much that you can learn on your Mac. There’s so much that you can learn on your Windows machine or any of the myriad of softwares that we use. What should you use? Because you can spend all of your time doing that.

So, my thing was, what is it that you want? And helping to translate a vision into what is it technically that we need to do. And let me teach you that, so you can just jump straight to what you want to do and understand the other elements involved and ignore the rest if you don’t feel like nerding out all day on all of the rest of the features. If you want to learn them, I’m here to teach you, but we can cut that out and just get you straight to what you want to do.

Justin Donald: Yeah, that’s awesome. Well, I think Apple has changed the game. And even from the standpoint today of like cloud-based storage, I mean, whenever I get a new computer these days, it’s just like, I can do it myself. I don’t even need the team. So, they’re brilliant in the fact that, like, the Genius Bar can be related to some other genius. It doesn’t have to be on the cloud transfer. I mean, it’s not a cloud transfer. It’s just bringing the cloud onto another device where you have everything stored. So, for me, it’s great. The cloud just captures everything. So, if I ever delete something, at one point in time, I remember it was like an external time machine and you could go back in time. And so, it’s kind of already built in, and I love it.

Shawn Lemon: Yeah, it’s so good now. And a lot of people still don’t have that quite yet. But this is one of the things that digital organization can do for you is you put your laptop on top of the car and then take off and it gets run over, you don’t worry about it. You just go and buy a new one. You sign into your account, and the majority of it comes down. You log into your one-password account and then you’ve got all the accounts and then you can just start logging back into everything and download the few apps that you need. And it’s no big deal. You just keep on rolling. You can pick up any device and just work and know exactly where to find things because you’ve got one source of truth for all of your files.

Justin Donald: Yeah, it’s brilliant. And the way that you would, for those of you that are iPhone users, you can set your Mac book up or your iPad or whatever, you can set it all up just like the iPhone where you get a new iPhone, boom. Everything uploads, all your same settings because that was stored in the cloud. And you can do the same thing on your Mac book, which has been a game changer for me.

This has been awesome, Shawn. I appreciate the time. I appreciate the deep dive into technology and digital organization and for you creating your company. Where can people learn more about you, for those that want to follow up and want to get their house in order?

Shawn Lemon: Yeah. So, the best thing to do would be to go to TheDigitalOrganizer.com/lifestyle, because what I’ve got for you is a file organization guide. It’s paired with videos, it’s very visual, and it’s got kind of the step-by-step process of this is the process that we take our clients through. So, if you want to self-implement or you want to check this out, that’s perfect. And then I introduce you to the company and more of what we do and give you a bunch of resources of how to clean up your email and everything. So, that is the perfect starting place is TheDigitalOrganizer.com/lifestyle, and then you can get all of that stuff and book a call with me if you’re interested in chatting. But yeah, that’s perfect spot.

Justin Donald: Love it. Well, I love ending our podcast with a question to our audience. So, every week, I ask the same question and hopefully, the repetition of this question is moving people closer to financial freedom. But the question is this, so those of you tuning in, those of you watching, those of you listening, what’s one step that you can take today to move towards financial freedom and move towards the life that you desire, a life that’s on your terms, so a life by design rather than default?

And what is the one thing that you can grab today from Shawn’s message, from Shawn’s tools that can help you get there, help you at least get into a position where you have some things in order to be able to move and focus on the financials? So, thanks for tuning in this week. And we’ll check you out again next week.

Shawn Lemon: Thank you.

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Justin Donald is a leading financial strategist who helps you find your way through the complexities of financial planning. A pioneer in structuring deals and disciplined investment systems, he now consults and advises entrepreneurs and executives on lifestyle investing.

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