Modern Entrepreneurship is easier than it has ever been. So, naturally, we make it as hard on ourselves as possible!
Today we’re discussing why we feel isolated, why we can’t seem to ‘get it’… and why we want to quit.
But first, have a look at this video I made for you!
The song was inspired by my friend and mentor at Maxwell Leadership, Chris Robinson. He’s the author of a book that has rocked my life – From Drift to Drive. But on a day in September 2025, he spoke to our Maxwell Mentorship group about how hard it is to be in this business, how lonely it can feel. I haven’t gotten permission to repeat all of that so instead for now, I’m going to reflect on my own painful journey. I wish this was a rosy, happy, let’s-go-conquer-the-world kind of post. But it is not. Well, at least not all of it.
Being an Entrepreneur is Lonely
Our Family Doesn’t Get It
It begins, often with a burden of knowledge or desire to help, often with a sense of shame. We struggle telling our family about what we feel we want to do – because after all, they are concerned about us. How could we NOT be part of the very industry-driven cabal that our education system has programmed us for? You work hard for 60 years and then retire. That’s the way of things… right? Don’t be upset with them. They are just looking out for you. In fact, I talked about this a few years back in this blog article – getting family support is great, but not required.
The issue I have had there is that it makes it feel like you’re wanting to keep it to yourself.
Then it gets worse.
Our Friends Don’t Get It
You start to realize pretty early into being self-employed or having a side-hustle that your friends are NOT who you should be pitching your products and services to. Sure, they want to be supportive in many cases – but in almost all cases they want to be your friend, not your customer. Everyone who has overwhelmed their Facebook with non-stop messages about their ‘new thing’ starts to feel eventually like they are shouting into the darkness.
Because they are.
Loneliness increases… isolation is our natural instinct.
But then it gets even worse.
Imposter Syndrome
This is one that kills my progress pretty much weekly: When you look at others that don’t seem like they are smarter than you… that maybe even do it worse than you do… but they’re making sales. You are not.
Or maybe you’re like me and you watch others that really have been doing it longer than you have, and they are so used to making everything look perfect on Instagram that they forget that it was hard for them too. They default to the image of having it all together.
The Myths of The SoloPreneur
Easily one of the things I loathe the most about doing this stuff is what I started to buy into, right around the time many of us did – 2015 or so. The idea that you could work for yourself, build a ‘business’ online, and finally be free to work when you wanted – from the beach! But maybe I’m jumping ahead. Let’s graze the surface with a few big myths that come to mind.
Myth 1: It’s Easy- Just Be Part of the ____ Movement!
By that time the obsession with selling products and services online had firmly taken hold. I won’t mention names here but several people figured out how to manipulate those with a desire and this sense of loneliness – all you have to do is buy their program for $4999 and you’ll have it made. Or just be part of the $97 per month membership and you’ll learn along the way. But you have to sign up now, on this call, before the price goes up! Others have stooped to convincing people to borrow money they don’t have, to use credit cards or “whatever it takes” because their system works!
But what drives the purchase? Almost without exception it is people tapping into this sense of loneliness. It’s disgusting.
Then there is what I’ve been encountering – the ‘guaranteed results’ lie. In 2025 alone, that one has cost me well over $25,000 because these people always figure out some stipulation or clause to keep their money. It’s disgusting.
The tactics still work today, but it’s causing many like myself to feel dirty even offering services. I don’t want to manipulate people’s emotions to make a sale – and that is keeping me from offering a lot of the time!
What kills me here is some of the tactics do work. And some concepts like a Mastermind and Coaching DO work… but so many are offering them, having no training or accountability. It’s just another sales funnel to them, but you hope so much for the result that you buy in.
Myth 2: Anyone Can Do It
First it was blogs, then books, then YouTube – but the message has always been basically the same: It’s so easy, anyone can do it!
I probably don’t need to say another word here, do I? If you have read this far you already know what I’m going to say.
You can’t do it.
There I said it. Or maybe… you shouldn’t do it.
I believe firmly at this point in my life that we were created with certain talents – God-given natural abilities – that others do not have. It was designed to let us all work together naturally. Along with these talents are Gifts – that our faith provides – that further enhance these talents into areas of passion.
The problem with the ‘systems’ I mention above is that they are the kinds of things that the modern enterprise has literally hundreds of people doing – but to sell the lie of being a solopreneur, you learn to do… everything… at least, until you can afford a staff to do it for you.
Seems logical enough except that it goes against the way we were made. Sure, I like knowing things but… doing things is quite different. I, like so many others, fell into the trap – hard.
You have to create a course. And write a book. And a membership. And start speaking. And do the marketing. And social media. And sales. And accounting. And taxes. And handle merchandise. And book coaching calls. And…
I digress.
The reality is that if you do everything not well, then everything sucks the life out of you- and then everything gets worse from there. Quality goes down, sure, but production goes down too.
What really burns me about this one is my own patterns here. I am so “GenX” that nearly everything I do is out of a sense of anger that I have to figure it out myself and do it myself and noone cares and I don’t get paid and… you get it, right? The hard part here is that buying into the lies about doing it myself for so long has made it impossible for me to delegate!
Even when I was doing well years ago and had the funds to hire out help – I did so badly at that it completely ruined my business. And that brings me to #3…
Myth 3: You Have to Be All In
At this point in my life, I make a horrible employee and I know it. I tried a few years ago. It didn’t work. In fact in 2017 I was fired for a blog post and I never looked back.
Yet now I see peers of mine back in those days that have a comfortable life. They make far more money than I do each year, take more vacations and life is easier for them than it was supposed to be for me.
Why?
Because of the lie that I should go “all in” on my business or it won’t work.
The sad thing is that at this point for me, that has become true – but I really REALLY wish more people would take the ‘side hustle’ term more seriously. Side. As in, when there is time. Hustle as in, not something you want to be doing long term.
This is rapidly getting into an area of coaching advice so I’ll just say here that I’m not giving you specific advice – you would have to engage with me separately for that. This is just my take on things in my experience…
If it were me advising younger me to be an ‘digital entrepreneur’, I’d say do NOT QUIT your day job until all of these are true:
- More Income coming in from your side hustle than your main job (seriously)
- AND you have 12 months of expenses in liquid funds (not investment, liquid)
- AND you have had at least one assistant helping you for at least 6 months
- AND you have at least 10 solid testimonials or reviews of your primary product
- AND you have a solid business plan that your spouse can understand clearly
- AND you have taxes and accounting out of your hands and done by someone accredited
How many of these things I do not have today is staggering. If I had not three times in my life been pushed out of being an employee and landing on working for myself, I wouldn’t do this.
In fact, as I’m writing this, I am treating ‘new things’ I want to do in coaching, leadership training, and speaking as ‘side hustles’ to my primary technology consulting. It is frustrating, exhausting, and confusing to everyone around me… but the above are my basic criteria for when I take the next thing full time!
What to Do About It
I have come to a single conclusion about the loneliness problem with Entrepreneurs/Solopreneurs. And that is that the business is not your problem. Your community is.
Jim Rohn said it long ago: You’re the average of the five people you spend the most time with.
Not who you like. Not who you choose or identify with. Who you spend time with.
Sometimes, we have to do the hard thing and cut people our of our lives. If they drag our average down, what is that going to do to the people we are trying to serve?
So – get into a community and spend as much time as you can there. For me, I have been doing this with Maxwell Leadership; pretty much every day I interact in that community – more than any other.
Find your crew, your tribe, your ride-or-dies. Make them a priority!
For the other strategies, I use a system of Four M’s for guidance to my tech community and it works here too:
- Mindset
- Mastery
- Methods
- Mentoring
These are topics for another day – but as I close out here I want to offer help if I can in Mentoring.
You’ve read this far – and hopefully saw the video, so I’ve taken a lot of your time… I’m willing to give some back.
The link below will allow you to book a half-hour on my calendar. If you need to talk thru something, figure something out – I’m offering this while I can do so. The nice thing is the more people I connect with, the better I can figure out how to help.
There’s no obligation or sales pitch or whatever. If I think we should talk again, I’ll offer it. If I think someone else will be a better fit, I’ll put you in contact if I can.
Yes, I do coaching and mentoring and yes I am paid for it – however, that’s something you’d need to pitch me on… we can talk about it but I’d likely require you to meet with me several times before we commit to that kind of relationship. I’ve been burned by coaching clients as well as coaches, and I gave up long ago on trying to pitch paid solutions on calls that aren’t meant for that.
MY ONLY ASK is that if you book a call with me that you take it seriously and show up. To be blunt: people not showing up for scheduled calls or not taking it seriously as a gift made me take this away for many years.
If you read this far – I’m confident you’re not going to be like that 😉
Here’s the form:
One More Thing…
I hope you got value out of this – I don’t blog often but this seemed appropriate today.
I didn’t even edit this, and probably should, but I hope being raw and honest was valuable.
If it was, would you please save this link?
When you find others challenged with these struggles – I would like you to send them this link!
Okay – one more “one more thing” 🙂
If you work with a team or a company and would like me to come speak at your company for a “Lunch and Learn” session about Leadership, that would be a great way to help me make this worthwhile! All I ask is that you help me set up an hour long meeting with a decision maker about staff training or coaching!
All I need to have you do is book a call above and let me know you’d like to talk to me about Lunch and Learn sessions!
I hope you have a wonderful day!
Be blessed by the best – then go be a blessing to all the rest!