“I don’t get why everyone is ‘making it’ except me!”
This is a common frustration among aspiring entrepreneurs and freelancers.
You watch enough Gary Vee, or you read enough Tim Ferriss, and you think that success is pretty straightforward: work hard, and you win!
In reality, it never works out that way, does it?
The most annoying part of this problem is that you can (correctly) look at these people who are crushing it and think to yourself, They aren’t any smarter or hard-working than me.
It’s true. Most successful people aren’t particularly impressive. I’ve met a bunch of them. It’s kinda shocking.
They all, however, put out a dangerous message: “Just work harder. Hustle more. Outwork the competition, just like I did.”
Don’t get me wrong. You won’t win without hard work.
But the Hustle Culture is a myth that needs to be taken out behind the woodshed.
Sometimes they realize it. Often they don’t. Either way, these gurus leave out certain data points that directly improve their efforts… and sink yours.
The dirty secret behind most entrepreneurs…
They’re single.
That’s really it.
Yes, there are exceptions. But most of them have very few “real life” commitments beyond their businesses.
It feels like a data point that shouldn’t matter. And yet, it does.
Think about your average day and ask yourself if the big-name gurus could handle the responsibilities that are a part of your routine:
- Making breakfast for your family
- Helping the kids get ready for school
- Exterminating rodents from your basement
- Feeding your chickens
- Meal planning
- Making dinner and sitting down with your family daily to eat it
- Driving your kids to swim lessons, band practices, and school activities in the evening
- Fixing your car on weekends
- Meeting with home repair contractors in the middle of the day
- Remodeling rooms at night
- Planning birthday parties
- Volunteering in church groups
- Reading books to your family at night
- Bath time for your daughters
- Baking bread and bagels for the week
You get the idea.
This is just a snapshot of some of the things I could think of off the top of my head.
I did almost none of these things when I was single and 20 years old.
Today, at 40 years old, with a wife and 4 kids, life is very different. That difference brings challenges to my business life.
The challenges they don’t account for
As adults with responsibilities, the Hustle Culture is a pure myth.
There just isn’t any logistical way to handle it because of these limitations:
- Time/schedule. “You should be working nights if you haven’t made it yet!” Okay, bro. I have to knock off at 4pm so I can make dinner, ask my kids about their school day, run somebody to swim lessons, and be present with my family. You might have a 9-5 job that takes up all your daytime, too! “Just work more” doesn’t always, well, work.
- Energy. We’re all only human. And at 40 years old, I’m turning into that dude that falls asleep in his recliner at 10pm each night. Sometimes I plan to do light work in the evenings after the kids are in bed, but I often find myself completely spent and can’t concentrate any more. Your body and brain need breaks.
- Investment. I would love – LOVE – to spend $1,000/month on software to automate every aspect of my business. And while I absolutely have to invest in my success (and I do), I have to balance out those investments with my family obligations, like unexpected purchases of new school shoes, or lawnmower repairs, or pest control, or any other thing like that. I can’t just blow it all on apps!
- Risk. At some level, you accept risk as an entrepreneur. But that risk is calculated differently when you’re single and living in a crummy apartment versus the head of a household of six with a mortgage to worry about. I can’t risk losing it all and putting my family out on the street. I have to weigh the pros and the cons first.
Reading this might feel like a relief, but it’s also the most critical moment.
It’s easy to see these challenges and feel validated, but true success comes from seeing them as conquerable.
The strategies that follow are a roadmap designed for your life – not theirs
You can succeed without the Hustle Culture because you have what the gurus don’t: real-world constraints that force you to be smarter, more efficient, and more focused.
Here are six different ways you can still pursue freelancing as a long-term, full-time solution… without resorting to “life hacks”:
Vet the guru
This is important.
What’s his/her vibe?
What image are they projecting? Is it one that you can realistically achieve? Or is it some bombastic personality flexing big cars, slicked-back hair, and luxury travel?
Personally, I’m turned off by these dorks almost instantly.
I don’t need all that. I just want to provide for my family and enjoy a pretty peaceful life.
And if you see a broccoli-headed haircut on the guru, RUN.
Don’t take life or business advice from a 20-year old who has no idea how the world works outside of Twitter.
Break everything down into systems
My brain has two modes: ‘Chaos Gremlin’ and ‘System Builder.’
When I learn something new, the Chaos Gremlin wants to immediately throw it at my coaching community like confetti.
But I have to wrestle it into submission, because I know you don’t need more confetti.
You need a system. A step-by-step process that works even when the dog is barking and a kid is asking for help with algebra.
When you are concerned about time and energy, your goal needs to be to work as efficiently as possible.
That’s what systems do.
By making everything systematic, I am able to run things on autopilot. I don’t worry about what to do next, I don’t have to make a lot of big decisions. I can just GO.
That’s huge.
Set boundaries on both sides
Whenever I bring in a new writer to my coaching community, I make one thing very clear:
You can DM me whenever you want. But it may not be replied to until the next business day.
Why? Because my nights and weekends are for my family.
I rarely have clients who try to take advantage of that time, but I have that policy nonetheless.
I became a freelancer to give me the freedom to be present with my family and be the dad I didn’t get growing up.
I’m not going to blow off my family time to work with a client.
That goes the opposite direction, too.
If I am working during the day, my wife and kids know that my Work Time is important, too. I need it so that I can provide for them.
Exceptions can be made from time to time. But they understand that they get Dad Time at night and on weekends because I get Work Time during the week.
Boundaries are beneficial for everybody. It helps keep a balance.
Set different expectations for yourself
The single guy who has $900 in extra spending money and works a remote job 4 hours per day is going to get results faster than the guy who has $100 in extra spending money, works a 9-5 in an office, and has a family at home.
It’s just reality.
If your expectation is that you’ll crush it out of the gate and make $10,000/month in your second month, I’ve got some bad news for ya.
It’s not that it can’t happen. But the chances are slim.
Instead, you have to start celebrating little victories.
No, you can’t replace your 9-5 in two weeks.
But if you land a client in your first month worth $1500/month? Hey, that’s something.
Even if you just book your first project for $500 – that’s moneymaking!
The definition of success changes.
Success looks different for us.
It isn’t a rented Lamborghini.
It’s the quiet confidence of knowing every bill is paid.
It’s the status of being the parent who can afford new school shoes without checking the bank balance first.
It’s building a fortress of security for your family, not just a flashy business.
Redefine your goals around that reality, and every small win will feel like the major victory it truly is.
Prioritize. Prioritize. Prioritize.
“How does he do it all?”
He doesn’t.
You can’t.
Set goals one at a time.
You’re not going to build a website, set up a cold email campaign to blast out at 500/day, build your portfolio, and launch a Youtube channel all in one week.
You pick what I call the biggest Needle Movers and focus on them.
One at a time.
Chip away at all your goals and eventually you’ll make your way through the list. But it will take time.
Embrace the seasons of life
Sometimes life feels like “Everything is coming up Milhouse!”
Other times, you can’t do anything right.
Sometimes, you’ll have plenty of time with family.
And hey, other times you have to focus on work.
All of these are okay.
They pass.
The seasons are what they are.
I have weeks where I sit down with my wife on Sunday night and say, “Hey babe, I’m going to be doing some work this week at night.”
And she gets it.
That’s because I set those boundaries and expectations regularly.
She knows that, if I lean into it this week, next week I’ll have plenty more availability and we’ll be back to normal again.
When you’re busy, you’re busy.
When you’re struggling to handle things, you have to lean in.
Just make sure everyone knows it’s temporary – and then it’s your job to make sure it’s temporary!
It can be done
Imagine what it would feel like to build a business that funds your life, instead of a life that funds your business.
Imagine closing your laptop at 4 PM, knowing you’ve done meaningful work, and then being fully present for dinner, swim lessons, and bedtime stories – without the gnawing anxiety that you should be ‘hustling.’
Forget Ferraris. You want freedom!
You can build this life.
Now if you’ll excuse me, I have to go calm down my baby daughter who is screaming in her crib as I finish writing this (seriously)…
