How to Stop Being the Freelance Business Bottleneck in Your Own Business
One of the biggest advantages of freelancing is that you don’t need a big team to build a business. But that can also become one of your biggest problems. When you are the business, everything depends on you — from finding clients and managing projects to answering emails, creating proposals, handling admin, and delivering the actual work.
In this episode of The Freelance Insider Show, Al Calder talks with entrepreneur and business coach Jordan Solender about how freelancers and solopreneurs can remove themselves as the bottleneck in their own businesses. Jordan shares lessons from building businesses since he was 13, including an eight-figure exit and multiple companies that now operate without requiring him to handle every task.
You’ll learn how to identify work that shouldn’t require your personal involvement, when to delegate versus automate, how to use AI as leverage without over-automating your business, and why documenting a process can make it much easier to hand off to someone else. Jordan also explains his 10-80-10 delegation framework, his “pick one thing and remove yourself” approach, and a simple exercise for deciding what task you should eliminate from your workload first.
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What You’ll Learn in This Episode
- Why successful freelancers can become the bottleneck in their own businesses
- Why being good at your freelance skill doesn’t necessarily mean you’re good at running a business
- How to identify tasks that genuinely require your expertise
- How freelancers can delegate without having employees
- When to use a virtual assistant, contractor, automation, or AI
- Why “nobody can do it as well as I can” can hold your business back
- How to determine whether a task should be eliminated, automated, or delegated
- Why bottlenecks are often system problems rather than motivation problems
- How to document repetitive tasks so someone else can take them over
- How to create useful SOPs without turning documentation into a massive project
- How Jordan’s 10-80-10 delegation framework works
- How freelancers can use AI to handle the repetitive 80% of their work
- How to test a virtual assistant without putting your business at unnecessary risk
- Why judgment and communication can matter more than technical skills when hiring help
- How the “pick one thing and remove yourself” sprint works
- How AI agents could help freelancers automate repetitive business processes
- Why freelancers should automate processes without automating important client relationships
- How to avoid over-automating your business
- What freelancers can do tomorrow morning to start removing themselves as the bottleneck
Episode Transcript
Why Can Freelancers Become the Bottleneck in Their Own Business?
If you’re sending six emails back and forth with say two or three clients to find a time bottleneck, >> right?
Right. That that right there, that’s probably an AI agent with a calendar integration.
One of the biggest advantages of freelancing is that you don’t need a big team to build a business. But that can also be one of your biggest problems.
Because when you are the business, everything depends on you. More clients can mean more money, but it also means more work, more admin, more emails, and ultimately less freedom. So, how can you go from being the person that has to do everything to figuring out that there are some things that you shouldn’t be doing at all and to ultimately grow a business that doesn’t consume all of your free time? That’s what we’re going to explore today with Jordan Sander, who’s helped founders identify and eliminate the bottlenecks that are keeping them stuck. Jordan has been building businesses since he was 13 years old. From a snowplow business to a DJ business in high school and ultimately to an 8 figureure exit. Today he helps business owners remove themselves as the bottleneck so that their business doesn’t depend on them for every little decision. Jordan, welcome to the Freelance Insider Show.
Thanks for coming today.
Absolutely, man. Thanks so much for having me.
What Does Starting a Business at 13 Teach You About Entrepreneurship?
I want to start off with uh probably an obvious question, but you started your first business at 13 with a snowblower.
Um what did that early business teach you about entrepreneurship?
So the de demand is everything first off, right? Uh if you you need to have something that or a service that you can offer people that uh were actively looking for, right? So, snowblowing in the winter is is a pretty obvious one.
But entrepreneurship uh right out of the gate though is a is really just getting comfortable being uncomfortable. And I I say that a lot. I say it to my employees. I say it uh to to my sales team, right? Like you got to be comfortable being uncomfortable. And when you first start a business, you think the job is whatever the business does, right? So if you’re a snowblowing company, you you think your job is to snowblow, right? If you’re a DJ, you think your job is DJing, and then you realize, no, your your job is sales, marketing, hiring, firing, cash flow, P&L monitoring, and customer service.
So, it taught me really early that uh being good at the thing doesn’t necessarily mean you’re good at running a business.
When Does a Business Owner Become the Bottleneck to Growth?
So fast forward that you’ve now built and exited an eight figureure business.
When did you first realize that you could become the bottleneck to your own growth?
So when when you’re exiting a a business of that size and you have you you typically have a lot of realizations. Um the uncomfortable realization is and we talk about uncomfort a lot. You’re going to find that’s a theme in in majority of my conversations is that the things that make you a great founder early on can make you a terrible CEO later. And early on, you being involved in everything is a superpower, right? Uh you you sold it, you solved it, you knew every customer, you knew every problem, every single number, and that works until the moment it doesn’t anymore, >> right? And at some point I realized people weren’t coming to me because I was uniquely qualified to make every decision. Uh I don’t have a background uh in in college like a business degree or anything like that. They were coming to me because I had trained the company to need me. And that’s a very different problem. Everything just relied on me.
So when we talk about bottlenecks, um the the one that everybody gets sucked into the most is the the saying nobody can do it as well as I can. right?
Or nobody else can handle this. I have to do it. And maybe that’s true. But if everything has to be done by you, you didn’t build the business. You built yourself a very stressful job with employees. And that shift for me was realizing the job wasn’t to have all the answers anymore. My job was to build people in systems that could produce great answers without me being in the mix.
How Can Freelancers Delegate Without Having Employees?
So you said this part about it, people thinking that they have to do everything, that they have to be the center of everything as a freelancer that’s obviously that’s they don’t necessarily have the network, they don’t have employees, they don’t have people working for them. What would you say to them >> for for the freelancers out there that are working? I’m assuming when you’re saying freelancing, you’re talking about people that are just working on their own, coming into a business to to try to help and solve problems, >> right?
Yep. Yeah. they’re working solving other people’s problems.
A lot of the reliance that in my advice to them is systems. Just because you don’t have a staff of 30 people deep and a bench of engineers doesn’t mean you can’t have systems. I think this the freelancers actually have to learn this lesson even faster than I ever did because there’s a ceiling on how much money they can make by selling their own time.
Right.
Right. And I challenge the idea that you need employees before you can delegate.
You don’t you you just really need leverage. And what I mean by that is uh a leverage for a freelancer could be a virtual assistant.
It could be a contractor that works for them. It can be an automation like an NN or Make.com or an AI agent today. Uh today it can it can absolutely be AI actually. So you can have a little army working for you without having a single W2 employee. And the mistake I think freelancers make is saying well I can do this myself. Right? Going back to the previous thing I was talking about of, you know, why would anybody else do it?
Well, of course they can do this themselves. That’s that’s the wrong question. They’re insanely talented and usually that’s why they’re freelancing to begin with because they’ve figured out that they have a specific amount of value where they get to go into different businesses or be hired on a one-off to solve very specific problems.
But my hot take on that is that doing everything yourself isn’t always hustle. Sometimes it’s just ego in disguise as you know work ethic >> right so why do you think so many entrepreneurs freelancers whoever have such a hard time letting go in it accepting that kind of thing
I get this one a good amount uh especially from friends who are freelancers I think there’s a few reasons though but ego is a bigger driver than most entrepreneurs reneurs want to admit, right? We we tell ourselves, like I said, that nobody can do this like I can do it.
Nobody’s going to do it exactly like you is usually my answer to that. But what took me a while to learn that was they they don’t have to do it like me. They don’t have to do it the Jordan way. In fact, I now looking back on it, you know, in in training people and as many staff as I have, I don’t want them to do it the Jordan way. I want them to do it the creative Lisa way or the creative KO way. And if somebody can do something 80% as well as me, but they can do it without me. So I get to reserve my time for strategy, that’s often infinitely more valuable to the business. And then the other piece of that is control.
When you build something from nothing, it becomes your baby.
Right.
Right. whether it’s a smaller freelance business or you know a a huge company.
So delegating feels very risky because you’re taking delivery, sales, finance, those things off your plate and you’re trusting somebody else with you know portion of your baby. But there’s a difference between delegating and advocating.
There’s a lot of LinkedIn, Instagram, you know, gurus that talk about this and it’s so frustrating to see out in the wild, but you got to give these people that you’re delegating to an outcome. The ones that are giving you le leverage, you got to give them that outcome. You got to give them guard rails. Give them authority to make decisions and then, you know, let them let them surprise you. Um because if you hire smart people and you make every decision for them, eventually the smart people leave and you’re left with the people who are comfortable asking permission and then you’re getting sucked into the again.
You just missed an opportunity was right there in front of you.
How Do You Know What Work Actually Requires Your Expertise?
How does someone tell the difference between what generally requires their expertise and what’s something that they simply are just unwilling to give up?
How do they make that differentiation?
So to differentiate on that there’s a I think there’s a really simple test uh if I always like to you know say to my coaching clients as well as uh clients in the AI business you know if you disappeared for 30 days what would actually break because only you could do it versus what would break because you’ve never taught anybody else to do it and I think those are two very very different things so founders what I’ve realized tend to confuse familiarity uh with expertise, right? Like I’ve always done the proposals. I’ve always talked to this client. I’ve always approved this. I’ve always run that report, but does that actually require your unique skill set, right? Or have you just never built the process to let somebody else own it? And I learned this really early on where I hired my first ever VA. Uh she’s still with me today.
Could not live without her. She know who she knows who she is. and and uh there were certain reports I would just get out every single week to to certain clients and certain documents I would get to them and it got to a point where I remember I was going on vacation a year or two after hiring her and she was like can I just do this because you know it’s either waiting on you or it’s taking up your time where I need you to be doing other things and I was like I I never really considered is this something that I need to do or is this something I never built a process around. So I usually put things in three buckets now that I’ve lived through this and I coach people on it. The bucket one is only I can do it right. It requires my unique skill set, my creativity etc. Uh bucket number two is somebody else can do it with training, right? So I can build a process for it. I can typically hand this off. And the third bucket, which is a newer one to this day and age over the past couple years, is nobody should be doing it because a system of AI should do it. And that third bucket is getting bigger every day, especially for freelancers. The people listening to this, they’re they’re that bucket should be probably one of the biggest for them.
Oh, it’s a it’s a huge equalizer, right?
Are Bottlenecks Really System Problems Rather Than Motivation Problems?
You’ve mentioned that bottlenecks um are really system problems and not motivation problems. Can you expand on that? What do you mean by that exactly?
You want an example?
Sure. Yeah. So, I think first and foremost, right, when you’re when you’re looking at one of these problems, I think we have this bad habit in business, whether you’re a freelancer, bigger business. I’m trying to talk to everybody here that when something isn’t getting done, we immediately blame the other person. You know, like the Spider-Man meme, right?
And you know, they need to work harder, they need to be more accountable, they need to care more. Why don’t they care like I care? Uh maybe, but if the same problem keeps happening with different people, you found the common denominator, right? It’s it’s the system. So, if leads aren’t getting followed up with, maybe your salesperson isn’t lazy. Maybe there’s no defined follow-up cadence, no automation, no clear ownership, or, you know, nobody knows what good actually looks like or what they should be saying to actually nail the sale and and win the follow-up, you know, and I’m typically looking at at four things when I’m talking about uh either automating or when things keep kind of boomerang boomeranging back to me, you know, is there a clear outcome? Is there an owner? Is there a process? and what’s the number that tells me whether it’s working or not, right? What’s the trend?
Where what are my leading indicators to know that this is the fix that worked?
And if those four things exist and somebody still isn’t performing, well, at that point, we have a people problem, right?
So, but the hot take here is accountability without clarity is just yelling with a spreadsheet.
It it doesn’t help, right?
So, you know, we we need the clarity like you said, trying to tie this on both ends. Um because there are freelancers who do, you know, they have virtual assistants like you talked about. Um so they do have a a bit of an organization, albeit a mini one. Um but for freelancers that don’t have employees, um what does removing yourself as a bottleneck actually mean for a solo freelancer, you think?
What Does Removing Yourself as a Bottleneck Mean for a Solo Freelancer?
I think a lot of it means just to get out of your own way, you know. Um I think it’s most important for a solo freelancer.
I think it’s I think it’s probably the most important for for a solo freelancer because you can be a bottleneck even when you’re the only person in the company. And I like to choose my words really carefully, especially for the freelance through the inserts, right?
Because what I don’t want them doing is just saying, “Oh, I’m just going to give my entire business to AI,” right? That’s that’s not the intention of of what I preach, coach, and practice. The the question isn’t just what can I delegate to another human. It’s what currently requires me that shouldn’t require me.
Right.
Right. Cuz I’m not saying delegate your entire business. I’m not saying go hire 40 or 50 people.
It’s it’s really just thinking what currently requires me that should not require me. So an example like take scheduling. If you’re sending six emails back and forth with say two or three clients to find a time bottleneck, >> right?
Right. That that right there, that’s probably an AI agent with a calendar integration. Right. Proposals. If you’re rebuilding every single proposal you’re doing from scratch, even if you’re using like chat GPT or Claude or some to use it, right? You’re still the bottleneck on it. So that’s that’s a great VA one. or client onboarding is is a fan favorite that I feel like everybody is still super manual on. Uh if every new client needs you to personally explain the same 15 things, here’s where you click, here’s where you sign in, here’s how you generate your results, right? Record it, document it, automate it.
Right. So admin, invoicing, all that kind of stuff.
Absolutely. Yeah. So, if somebody’s watching this right now and they’re in that boat, they’re a solo freelancer, um, but they don’t really know where to start, they’re not sure what automation to start with, what would you suggest to them?
What Should Freelancers Automate First?
Well, like we talked about with those those three buckets, they’re we’re trying to figure out, you know, which which things should be handing off, which things should be automated or AIDed. Um, I would tell them don’t start immediately automating everything. Start with what is annoying them, right? for the next week. Every time you catch yourself saying, “I hate having to do this,” or, “Oh god, I got to generate these invoices again.” Right?
Write that down. This is your automation list. We’re going to start building it together.
You know, uh I say that’s my clients.
That’s like the first two weeks that we’re working together. So, don’t try to automate your entire business on day one. You want to find the thing that is repetitive, that is frequent, and that is low value, and then start from there.
And I mentioned scheduling earlier. So, scheduling is a very easy one. Follow-up emails, invoicing, client onboarding, taking notes from a call and then automatically, you know, uploading them to your CRM because your AI noteaker is connected, creating the first draft of a proposal, right? None of those things need creative genius,
right?
They’re they’re easily automated. They are very repetitive and every single freelancer is doing it already. Uh, so the fact that you haven’t automated that that that’s that’s where exactly where I would start with your automation, right? Because it’s I mean it’s so easy to go down that rabbit hole, right?
You’re trying to do seven things at once and I want to automate this and I want to automate that. So I I think it boils down to what you’re saying is just keep focused. Don’t try to do everything at once. Right.
How Can Freelancers Document Tasks So They Can Delegate Them?
100%. So, we talked about it a little bit earlier, but I I kind of want to go back to you said, you know, these people that say, “Well, I don’t want to delegate to anybody else. I’d rather just do it myself. It’s so hard to teach someone to do something.” What do you say to them?
If you can document it, you can delegate it.
That’s it’s the simplest thing. If you can document it, you can delegate it.
And some sometimes um I’m gonna agree with the freelancers that because this could be ego, this could be, you know, a bunch of different things. I will I will give them a little leeway here. I’m not just like this documentation pirate. But sometimes it is faster to do it yourself once, right?
But the problem is every single time I admit that to a freelancer, then I they follow it up with by saying, “You’re not going to do it once though. you’re going to do it another 500 times that you’re a freelancer. And I think freelancers will calculate the cost of training completely wrong.
They’ll say it’ll take me 3 hours to teach somebody this and then I can do it myself in 20 minutes. Great. But if it’s a 20inut task and you have to do that three to five times a week, that’s I don’t know like 40 50 hours a year, right?
Right. You’re you’re spending time on something because you didn’t want to invest 3 hours up front. That’s a terrible trade. And if you’re a freelancer, your time is everything. You know how valuable your time is. You’re charging by the hour for your time usually, right? In 90% of freelancers, that’s exactly how you charge,
right?
And next time you’re doing the task, you know, just record your screen. I will challenge you. Record your screen. Talk through it on the microphone. What you’re doing, why you’re doing it. I’m clicking this because of this and this is the context. And then go ahead and just give that recording to somebody and and have them just watch it and ask questions. And whatever questions they ask, you redo the recording. You include the answers. And that’s how you handle fringe cases and you just keep running it back until it’s a perfect SOP.
Kind of force yourself to look at yourself in the mirror almost. That’s what the recording is doing, right?
100%.
Makes sense. So you talked about documentation.
How Much Documentation Does a Freelancer Need Before Delegating a Task?
So on that topic, how do you know when you have enough documentation that you can actually you’re ready to hand it off to somebody?
Like is it just I’ve done it once, I have a small process or should you really dive in a bit deeper before you start handing off?
Yeah. And when you start going down this rabbit hole of documentation, entrepreneurs for some reason think that as soon as we they hear the word SOP or operating procedure, they think that their SOP has to look like a NASA launch manual or something. So the test is so simple. Can a reasonably competent person who has never done this before get the right outcome without asking me a question? Right?
It’s it’s so simple.
If yes, you’ve probably documented enough.
And I like letting the person uh I’m delegating to almost finish the documentation. And I’ll record myself doing something. I’ll explain why I’m thinking and why I’m thinking it. And then I’ll hand it over and I say, “You build the SOP.” I’ve done that with my assistant so many times. I’ll run through a finance report. I’ll say, “I’m clicking this because of this. I’m clicking this because of this.” And then I run this report because I think the customers love seeing that. And then I actually hand her the video and I say, “Can you make an SOP out of this for me?” And I review what she comes back with, what her takeaways are from the video. And then from there, I can even critique even further. And that actually accelerates the process, which is really nice. So, um, long answer, but the documentation shouldn’t be this giant project you finish before you delegate anything, right? delegate earlier and then you can kind of let the reality of the person doing the task expose the gaps of what’s missing there and prove it as you go.
I think people kind of overthink it.
They put put too much into it.
Oh yeah. Oh yeah.
How Did Delegation Help Jordan Build Businesses Without Doing Everything Himself?
So what about a specific example like kind of back to when you first started doing this kind of thing? Can you think of a you know one of those first times when you actually delegated for the first time you had that documentation?
so many times. So, so so much of this, so much nonsense task that I’ve handed off. Um, okay. So, my one of some of my earliest examples, I don’t know if you saw in my bio, so one of my my passions, I was a I was a wedding DJ in Barnab Mitzvah DJ in in college and in high school. And I still own a few different DJ companies today. uh all in they they’re all uh they’re they’re all each individually, you know, in their own right seven figureure companies. Uh they do anywhere between a,000 to 3,000 events a year.
Um weddings, barb mitzvah, photo booth, corporate events.
And uh in those businesses when I started, I was literally doing everything. I was selling the event. I was planning the event. I was figuring out the timeline. I was coordinating with the venue. I was making sure the equipment was ready. And then I actually showed up and I DJed the wedding. And it was so much work. And the terrifying part about the whole thing, uh, well, for a wedding specifically, I’m sure you can imagine, right? You don’t get a freaking doover.
You get one shot, man. These people are getting married, so you get one shot.
So, you don’t get to redo the wedding.
And if somebody screws up a spreadsheet, a timeline, it you’ve got a you got a you know, lifetime event of somebody remembering like you up.
A lot of pressure.
A lot of pressure. So that forced me to really figure out in my head, you know, what equipment needs to be packed every single time?
Can I hire somebody to help me delegate that? Right. Right.
Uh when do we arrive? What questions need to be asked beforehand? What’s the backup plan when something goes wrong?
And once I started really turning the gears on the things that I did ask every single time or the things I did check or prep every single time, those turned into checklists, those turned into process and somebody else was slowly able to deliver the same experience that I was delivering, you know, just just on the operational part. And that allowed me to put in a director of operations who asks these questions, puts together these timelines, communicates with all the clients and the venues days and weeks and months ahead of time. And before you before you know it, once you start walking through this either on your business or your freelance, you know, role, you don’t even know it yet, but you’re building institutional knowledge, right?
Not trying to give it a fancy word, but that’s what it is, right? Like if you own a if you’re a freelancer and you have a VA and you’re walking through your own repetitive tasks and you’re writing them down, bravo. You are creating institutional knowledge that will that will go beyond you that’ll allow your business to grow.
What Is the 10-80-10 Delegation Framework?
So I just curious, do you still make guest appearances with with the DJing?
Do you go and do it yourself sometimes?
You know, I have I have equipment. Uh, so I have three boys under the age of 6 years old and ever since my second was born, I have not DJed. So it has been the fact four years now since I’ve done it. You know, I I think it would be like riding a bike. I mean, I did it for 17 years. Like when I met my wife, you know, all of her friends thought that she had a boyfriend in Canada because I was never around on the weekends.
Was always DJing a wedding. So, you know, I I don’t I think I could pick it back up again pretty quick, but no, I haven’t done it in many years.
Any budding DJs in the house there?
Yeah.
Uh, I got some funny Fisher Price toys and and stuff on Instagram if you follow me there. They they they love playing with the DJ toys.
Nice. Um, I want to talk about some of the the frameworks and systems that you’ve developed. Um, one you talk about is the 10/80/10 framework. What is that and how can freelancers apply that?
That’s a fun one. Uh, so 108010, not not something I developed. Uh, that’s been around since the 80s. I have my own version of it.
Um, just to, you know, but it’s it’s probably one of the most practical delegation frameworks known to man because it solves the biggest fear that people have, which is uh, if I delegate this, am I going to lose control of the quality?
Right? That’s what most people think, right? If I if I delegate sales then I I might lose the sales. I might lose the quality. If I delegate customer service, you know, the customer is still going to like our product. You know, what happens there? So, the answer is no, though. It it doesn’t compromise quality. And the reason that it doesn’t is it’s all in the way that the framework is set up.
So, you don’t actually remove yourself completely. You remove yourself from the middle. So, in 10/80/10, the the first 10% of it is me. Okay? I define what we’re trying to accomplish. I define what good looks like. I put together the guard rails. Maybe I even give examples of, hey, here’s how I would approach this.
Here’s how I would do it. And I make sure we’re solving the right problem or delivering the right experience for the customer.
Okay.
From there, I actually hand off the 80%.
That would be either the research, the building, the writing, the organizing, or the executing. Whatever the actual work is, that’s what’s being handed off.
So then I could actually come back for the final 10%.
Okay. So I set the vision right the middle 80%. Somebody else doing it or AI is doing it. I come back at the final 10%. And I’m reviewing it and I’m adding my judgment or my creativity. I’m making corrections and ultimately I own the output. It’s it’s very much a human in the loop situation. if it’s AI or if it’s with my team, right, I’m I’m overseeing it for probably a certain point until I completely trust that they they got it covered, right?
How Can Freelancers Use the 10-80-10 Framework for Proposals?
I’m trying to relate it all back to the freelancer model, right? Think for a freelancer, think about a proposal. You don’t necessarily need somebody else to decide your pricing or strategy, right?
That’s your first 10%. You’re deciding that. But do you need to spend an hour formatting it or pulling case studies together to support your numbers or writing boilerplate marketing jargon, putting it into the template and then even sending it? Probably not, you know, probably not.
Then you come back at the end, you review it, you personalize the important pieces and you hit send. And in this, you know, situation, AI, you know, can make 108010 ridiculously powerful.
because the 80% doesn’t even necessarily acquire another human anymore, right?
So, I I was talking to somebody uh the other day who is actually a freelancer. He does he does cold email as a service. Okay.
And he he is a high performer. You know, I run a I run across um a lot of freelancers that are very high performers, right? Have 20 30 clients. It’s just them and a virtual assistant and they’re just crushing it, just working ridiculous weeks. And I was telling him the other day that, you know, most high performers aren’t overwhelmed because they have too much work, right?
They’re overwhelmed because they’re doing too much of the 80%. And what I was working with him on was how to hand off that 80% so he can continue to perform at the level he’s performing at.
Otherwise, he’s going to burn himself out. So, they’re typically not burned out. And I think you would agree, you know, the the high-risisk performers, they’re not usually burned out by having too much vision or taking too many clients. They’re burned out by doing the majority of the the busy work >> in the middle of a task or or a project, right?
Yeah.
How Should Freelancers Hire and Manage a Virtual Assistant?
So, you talked in there about quality. So, I want to jump back to that. So, for a freelancer that is considering taking on a virtual assistant, there is obviously there is concern about quality online, right? How do you know who you’re hooking up with? What kind of approach would you take to that if you’re a freelancer starting to think, okay, maybe I do need to look into this virtual assistant idea?
So, is the question like what what would you do to make sure you’re getting the right person to maintain quality?
Yeah.
Oh, okay. Got it. Okay. Just making sure. Um, yep. So, I think the mistake here is before I launch into an answer is is treating a VA hire like you’re getting married. You’re you’re not. You’re you’re dating, right? This isn’t like a business partner. This isn’t like a cap table decision, you know? So, you don’t you don’t hand somebody the keys to your business on day one. You’re you’re not doing that with a VA. You give them a small low-risk paid project and you see what happens, right? You make sure that the outcomes are set ahead of time. You tell them your vision and what good should look like. You decide the guardrails and you come back on the end 10.
And I’m looking at a few things beyond whether they technically completed the task. I’m looking to see did they communicate? Did they ask intelligent questions? Did they asking questions when they were confused or even had them? If somebody comes to me and they’re fresh off the boat into my company and they’re asking me zero questions in the first week, red flag, right? like I want you to ask questions, right?
Um did they hit a deadline? Did they catch things I didn’t tell them to, right? Uh and and I would hire for judgment and communication before technical skill all day for a lot of these roles. I I can teach somebody my CRM. I can teach somebody how to run a financial report in QuickBooks. It’s it’s much harder to teach somebody how to give a about my customers, right?
So then from there you know once you have given and dated a little bit and given those little lower level tasks and they’ve executed well you gradually increase access and responsibility.
Maybe week one they’re doing research then they’re preparing something for you either personally or in the business for you to do whatever it is you’re doing.
Maybe then they’re touching client-f facing work and you’re creating you know that trust ladder. So, you know, with every week, you’re giving them more and more uh both responsibility, access, and purpose.
Okay.
So, but on the safety side, you know, use use common sense. Separate login, password managers, appropriate permissions. Your VA probably doesn’t need your social security number, bank password, and launch codes on on Tuesday morning.
That should be a red flag for sure.
Yeah.
Yeah. So, it’s a peacemeal approach. Just little small tasks to start off with. get comfortable and and see if the relationship’s working.
Basically, makes sense. Um, okay. So, I want to jump over to the other one. I I don’t know if I got this right, but I think you call it pick one thing removal sprint. How do they know what thing to remove from their process?
How Does the “Pick One Thing and Remove Yourself” Sprint Work?
Yeah. So, I think you’re referring to the uh pick one thing and remove yourself sprint.
Yes, that’s it.
So, pick one thing and remove yourself.
So uh when we decide we want more freedom as entrepreneurs and we’re suddenly rebuilding a CRM and hiring a VA or implementing AI or documenting process and building SOPs and handing things off. Somehow we’ve created more work trying to do less work.
Yeah.
So I tell people keep it really simple.
Look at your week and pick one recurring thing you never want to do again. Just one. Don’t pick two. Don’t pick three.
Don’t pick something that isn’t recurring. Pick one recurring task that you never want to do again. And then let’s from there create the documentation in order to hand it off.
Okay.
Okay. Pick one thing and remove yourself. And if you do that every week or just an 8week period, your life is going to look so different between now and 8 weeks from now. And I usually look for three characteristics.
uh when I’m picking that thing, I do it frequently.
It takes time and it doesn’t require my unique judgment, right?
Okay. Payroll is a perfect example of this, right? You’re not typically you’re not paying somebody like a VA or somebody like a subcontractor a different amount every single week. We have set rates, we have hours, right? we have projects. Uh, repeatable business scales. If you’re doing something manually every single time and it always lives in your head, freelancers, this is for you. That’s typically not scalable.
You’re capped. Try to make it repeatable.
Once you figure out what that thing is, then you give yourself a week or two to remove yourself from it. And maybe you automate it, maybe you document it and then delegate it to a person. Maybe AI handles 80% of it and then you check it before it goes out the door. I really don’t care how. The goal is simple though and that is this used to require me and now it doesn’t.
Right?
Go pick your thing.
How Can a Freelancer Decide Which Task to Remove First?
You you kind of hammer on it a lot. What’s important is it’s not to get overwhelmed with these things, right?
Just pick one thing at a time. Take, you know, baby steps and keep moving forward.
Yeah. You know, the the goal here is just to do one thing a week, not do three, not do five. And if you do that for a year, you know, you remove yourself from 52 things. You do it for eight weeks, you remove yourself from eight things and your weeks and your business will look vastly different.
Keep it simple.
So freelancers wants to start this this week and they want to remove one thing from their plate. What would you say to them to help decide what that one thing should be? You mentioned, you know, something simple like invoicing or just something that speaks to automation. Is is that the best approach? It it doesn’t need to be around automation. Remember, we we’re trying to figure out is this something that shouldn’t require you at all, that could easily go to another person, or that could not require any sort of person. So, I I’d actually tell them don’t start with what’s easiest to automate. I’d start with whatever is stealing the most time or energy.
And there’s there’s a difference here.
So, uh, I I do this exercise with my coaching clients. I say, you know, take a piece of paper, make three columns, and the first column is, I hate doing it. I do it repeatedly. And the third is someone else or something could reasonably do it, >> right?
Whatever shows up in all three columns is your first target.
It’s a dead giveaway.
Yeah, it’s a dead giveaway. And again, I’m gonna come back to payroll. I’m going to come back to scheduling. I’m going to come back to proposals because freelancers, these are things you’re doing on a daily basis. Don’t ignore it.
And the fourth and final question is right before you pull the trigger.
Does this interrupt revenue producing work? Because I’m doing this. Am I not a out there and able to respond to say more Upwork messages if you’re an Upwork freelancer, right? or cold call because that’s how I build websites and find people to talk to or call government contractors because I’m a sub and I freelance for technical work. You know, these are all different roles, right?
But if you’re doing the 80%, the thing that is repetitive on a weekly basis, is it stopping you from making more revenue? If the answer is yes, then start there.
How Can Freelancers Use AI Agents to Save Time?
We touched on automation. Um I want to go back to that. Um, where do you see AI creating the biggest opportunities for freelancers to get themselves out of the weeds? The ones that are sitting there stuck, you know, maybe they’ve done some of what you’ve suggested. They’ve looked at the the payroll and they’ve looked at things like that and they’re still not moving the needle as much as they’d like and they want to look at AI and automation. Where where would you start with that?
There’s so much and it’s moving at such a fast pace right now. I’m gonna try to make this easy and also say something that would will hold regardless of when they watch this because it’s literally weekly as you know, right? Things changing. But I think the biggest mistake though freelancers make when using AI is using it like a smarter Google search or a copywriter. And that’s useful, but the opportunity is using AI as labor. So AI agents as a um as a concept isn’t going anywhere. It’s just not, you know, 10 years from now, it’s still going to be around. And I would look at your business and ask, where am I moving information from one place to another? Uh, making the same basic decision repeatedly or creating the same type of output over and over because that’s where AI agents could really get interesting.
And I’ll give an example for the freelancers out there. And I’m going to try to, you know, I’m just going to pick sales because you’re all doing this to do capture of new business and business development. So, let’s just say you finish a sales call. AI can summarize it. AI can update your CRM. AI can track your follow-up, create the proposal, identify any sort of action items, and then schedule the next touches for you.
You shouldn’t finish a 30-minute call and then spend another 30 minutes doing administrative work because you had the call.
That’s that’s lowhanging fruit for anybody out there.
Okay. So, do you have favorite tools yourself that like make.com or you’re using claude chatgpt? Like where’s your flow right now?
My flow with AI tools again changes not so much week to week but month to month. Uh making websites and just basic very basic web apps. I love lovable.dev.
If you know uh Replet, B44, they’re all very similar but I I prefer Lovable.
They were the first on the scene. and I I liked working with them a lot. Uh for database work, I’m using Superbase.
For actual AI agents, I’m typically using a Hermes agent. Um tried OpenClaw security wasn’t, you know, secure enough for me. So I I prefer the Hermes framework and setup for security.
And if I’m doing just pure automation and just need light AI involvement or enrichment, I’m typically using N8N.
I’ve seen some videos on that with N8N.
Seems like a bit of a larger learning curve compared to some other things like maybe Google AI Studio or things like that.
I mean, if if you’re just getting started in automation and you want to just understand, you know, what the possibilities are, uh, Zapier does a fantastic free course and certification.
So, fantastic free course and certification. I’m pretty sure you can get through the whole thing in, you know, say two to three days if you really are just want to sit down. No, it’s not overwhelming at all. It’s it’s very very like base level baseline on the terminology and teaches you how to make your first couple automations.
I’ve actually put a couple couple team members through that training and certification just to just to understand automation and not even use the platform. You could take that to somewhere else, you know, and get a little more complicated.
How Can Freelancers Avoid Over-Automating Their Businesses?
What about overmating? People are so excited about AI, right? And you know, it’s scary for freelancers in some way.
They think it’s going to take their job.
But there are other freelancers who look at it totally differently. They go, “Wow, I can automate everything. I can get myself a million clients.” To freelancers like that that are kind of overmating or use AI when they shouldn’t. What would you say to them to get them to step back and take a look at the bigger picture?
Well, first and foremost, when I get asked, um, is AI going to take my take my job?
AI is not going to take your job.
Another freelancer with AI is gonna take your job, right? because they you know why somebody reaches out and you know says hey send me a quote on you know these three services and the freelancer that’s getting back to him in the first say five to seven minutes and then books a call takes that deal right it’s the reason why Amazon is so popular right you can get things same day next day within two days it’s right there it’s ready for you know we have short attention spans in this day and age and I think we’re going to I think we’re going to see a lot of people automate themselves though to your point of overmating into mediocrity because everything will just look the same. So, you want to have a nice blend of creativity and personalization in with the speed. And I know we’ve been talking a lot about AI, but just because AI can do something doesn’t mean AI should do something. That’s why the second bugget of of of the task handoff isn’t just should a person do this. It’s can I give this to another person that can effectively do it >> up to 80% as good as I can. And my rule is automate the process, not the relationship. So if I’m a freelancer, AI should absolutely help me research a prospect, prepare for the meeting, draft the follow-up, organize my notes, um and handle any sort of the administrative work. But AI should pre not pretend to be me building a relationship with my biggest client. You know, uh the what what really kills me is when I see business owners using Claude in their inbox and Claude is responding to me and I’m just like I’m having a conversation with a robot like let me let me feel you. You know, that that drives me nuts. I typically don’t work with those people very long.
Yeah. I I think it’s it’s so easy for people, right? And they’re looking at it. they’re going, I’ve struggled so long and maybe they’re not uh their freelance business hasn’t taken off the way they want and the thing this is the easy way out where I think probably the better response like you said is to pick your the lowerhanging fruit just to stay consistent and build your business and not be in a rush I think. Right.
Yeah. Yeah. So, you know, takeaway on that one is you know efficiency is not the goal in that situation. Value is the goal. efficiency is just how you create, you know, the room to deliver that value.
What Should an Overwhelmed Freelancer Do Tomorrow Morning?
Just a couple more questions for you Jordan. Um, so for a freelancer listening right now that feels completely overwhelmed and they realize after listening to this podcast episode that perhaps they are the bottleneck in their own business, what should they do tomorrow morning to get started?
Well, first off, don’t forget to like and subscribe this podcast.
You should absolutely be doing that. Um, and if you haven’t done that and or you if you’ve already done that, uh, don’t buy software, don’t hire somebody, and don’t build an AI agent. Just open your calendar, look at the last two weeks, and ask yourself, said it earlier, right? What did I spend time doing that I should have never been doing in the first place, right? And then pick one thing, not 10, just one. And then ask three questions. Mentioned it earlier. Can I eliminate it? Can I automate it? Can I delegate it? And I want you to ask them in that order. Because the best process sometimes isn’t better process. It’s realizing you shouldn’t be doing a damn thing at all.
Then block an hour tomorrow to actually remove it.
Okay? We don’t want to fill that hour back up with more busy work. We want to build fill that hour now up with revenued driving work with things that make the needle move.
So that is something you could do tomorrow on your own.
What Does Jordan Solender Do and How Can Freelancers Work With Him?
I read there in your bio that you’re doing business coaching and that which might be some freelancers might be interested in that. What’s tell me a little bit about that.
Yeah. Um, so right now I I have currently eight businesses running. Uh, all of them are under my purview. I have a couple uh transactions probably coming up to to slim me out on the business portfolio side. So, we’ll have a couple more sales coming up here soon. But for the most part, I’m spending my days doing um IT consulting, CEO coaching for both freelancers and like I would say startup CEOs. And then finally on Solander AI. So, I started an AI agency for uh a lot of the questions that you’re asking me uh people kept coming to me for and asking for help. So, we started an AI agency about eight months ago where we’re actually building in uh systems, processes, and pretty much anything that you could possibly dream up with AI. So, that’s that’s been a lot of fun.
How Can a Freelancer Know When Their Business No Longer Depends on Them?
What’s the ultimate test? How can a freelancer know that they’ve actually built a business that doesn’t depend on them for everything?
So to know when you’ve removed all the bottlenecks and the business doesn’t depend on you to run itself, can you step away for 30 days?
Okay.
And nothing break.
If you can step away for 30 days and it doesn’t break, that’s awesome. You have a battle necklace business. That’s fantastic. You should be able to only focus on at this point how to build more revenue, business development, and true CEO time. If you step away for 30 days in one thing to 10 things break, those are the things you got to work on.
Well, I want to thank you for coming on, Jordan. It’s been enlightening to say the least. Um, if people do want to reach out to you, how can they get a hold of you?
Yeah, absolutely. They can reach me for for AI. You can reach us at solander.ai.
my last name.ai uh for business coaching Jordaner.com.
Um yeah, please feel reach reach out any and all uh Instagram, Facebook, Tik Tok, LinkedIn, wherever you want to reach out to me. My team is monitoring. We’re ready. We’re here to listen. We’re ready to work with you.
Perfect. Thanks again. I appreciate this.
Yeah, absolutely. Thanks so much for having me.