The Advantages of Starting a Business after 40 |

Gary Vaynerchuck, James Altucher, Pat Flynn* and (insert favourite thought-leader here) will tell you that you don’t really need a traditional job anymore, and I tend to agree with them. I would agree though because I haven't had a real job in 10 years.

But like anything, it's not as simple as that.

Spend five minutes on Instagram and witness the 20-year-olds preach about following your passion, leaning into your strengths and blazing your own trail. “Travel the world in a van!” they say. “Manage social media accounts for clueless fortune 500’s and make bag loads of cash while you travel!”

It all sounds wonderful.

I recall Gary himself pleading to the crowd at a live event: “…please, please, stop doing sh*t you don’t like. You don’t have to do that anymore!”

Hell, I reckon if I were still 22, I’d be thinking the only thing I need to do it quit my job, live anywhere I like and join the new rich! Oh no, hang on, that’s from Tim Ferris’s book…

Yes, I know I sound cynical, but I have so much of this stuff swirling around in my head, I sometimes wonder if my thoughts are my own anymore.

And I bet some of you are thinking the same thing. If you’re over 35, you probably think most of it is nonsense. That’s because, like me, you’ve been around. You’ve actually done things. You’ve made children, got married, and you have a job and a mountain of bills to pay.

But like those viral posts that lead you down an hour-long rabbit hole (when all you were trying to do was Google the correct spelling for ‘emancipated’), you still find yourself wishing it were all true.


There's Good News and Bad News

The bad news is, you’re not a young pup anymore. You don’t have endless blocks of free time to sort the wheat from the dross. Your job drains the life out of you. You don’t have the energy you once had. That old flame called ‘purpose’ is more like a pilot light these days.

You’ve got scars, and you’re jaded. You're scarred because you’ve tried to break out before and failed, and you're jaded because it’s easier to accept your station in life and tell yourself things will never change for you. There’s just too much going on in your life to risk dreaming again.

But let me tell you, in your middle years, a perfect storm is brewing. Part of the story is the dreaded midlife crisis, but that’s more a disruption to the storm than the storm itself.

What I’m talking about is the convergence of three powerful elements:

  1. Experience
  2. Perspective
  3. Scars

There are plenty more, I’m sure, by I like the number three.

Notice anything unique about these? None of them can be bought or faked. They have to be lived. If you’ve made it to the other side of 40, you have each of these in spades. That means you have the most valuable asset you can bring to the table.


You’ve done stuff, seen things, and been damaged along the way. You’ve had highs and lows, victories and failures. And because of all this, you have things to offer those who are coming up behind you.

You are, without question, expert enough at something – probably a few things.

This puts you in an enviable position. Seriously – the 20-something’s with stars in their eyes don’t have what you have.

So this is the good news.

A twenty-year-old might have go-all-night levels of energy, but he has precious little real-world experience. He hasn’t tasted failure or disappointment or responsibilities like you have.

She doesn’t understand the value of the long game. Her mind is unfettered by the struggles of midlife, or divorce, or demanding teenage children.

These real-world challenges of yours offer enormous advantages. You’ve earned your scars. You have experience, perspective and insight into things they won’t know for decades to come. And you can use these to carve out a place for yourself and build a global audience for that something you have that no one else does.

Think about your career/s, your skills, your natural talents and the things you love to do – even if you barely get time to do them. There is stuff you know, things you’ve done, perspectives you have and wounds you carry that people want to hear about. Not your uncle or your sister, but other people.

Remember, we’re living in the most opportune environment we’ve ever known. For the first time in history, it’s possible to reach over three billion people using a simple little blog. The rise of smartphones and social media amplifies this to a scale unseen before.

Best of all, even the most narrowly focused topic can appeal to thousands – perhaps millions – of people.

Not long ago, I met a young woman at a YouTube conference who was making an excellent full-time living from modifying dolls and posting videos of the process she followed. Really. She even had an agent.

Regardless of what you do for a living; no matter where you are in your life right now, there is a special niche just for you. It needn’t be unique or particularly appealing to the masses because the uniqueness and the appeal will be YOU. Your perspective. Your voice.

Let me give you three wonderful assets you possess right now.

The Holy Trinity

For one, you have limited time (both genealogically and practically). That means you can’t faff around with six ideas at once. You need to focus on one thing at a time because, frankly, there’s only so much you can do after you get home, kiss the wife, kick the dog, hoof down dinner and help your kids with their homework.

This is a very good thing. It means you’re not like a puppy chasing its tail. You’re methodical, deliberate and purposeful. It also means you’ll likely pay for tried and tested advice and follow that advice to the letter. This propensity to focus your effort puts you way above the youngins who are prone to ‘new shiny’ syndrome at every turn.

The second advantage in your arsenal is the desire for a better quality of life. You don’t just want the money. A pool full of bikini-clad women and a garage-load of Italian thoroughbreds would be nice, but…meh, that’s not really you. And besides, you wife would probably leave you, and your kids would start calling their mum’s new boyfriend, “Dad”.

What I’m saying is you’ll probably pursue entrepreneurship for the ‘right’ reasons. And that, too, is a very good thing. It means your actions will have that all-important ring of truth. And in today’s celebrity/fake sincerity-saturated world, that’s as bankable as money. It means you’ll attract quality customers, powerful allies and great collaborators. It sets you apart from the wannabes.

The biggest thing you bring to the table, though, is your story. Because you’ve been here a while and done a few things, you actually have a story; you don’t need to make one up! You can be completely yourself and be almost guaranteed of finding enough people who resonate with your story.

My story, for example, is of someone who’s tried and failed at many things.

I’ve made money and I’ve lost money; I’ve married, and I’ve divorced. I’ve suffered debilitating setbacks, and I’ve endured a full-blown midlife crisis. But I’ve also triumphed and broken through the fog. I've travelled around the world and had at least six different careers. I’ve zeroed in on a few things I love, and these days, I live an autonomous and fulfilling life.

The reason for that is, I’ve found a few intersections between the things I enjoy, the things I know and the things I’m good at – and I’ve made a life out of them.

You can do this too.

Yes, you must respect the constraints of the season you’re in, but don’t let them stop you from formulating plans and taking consistent action towards the life you want.

In the 1979 Muppet Movie, Kermit said, “Life's like a movie; write your own ending.”

Be yourself, stake your claim, and go do something extraordinary!

The great thing today is, you needn’t throw out the baby with the bathwater. You can keep your miserable job and build something on the side. You don’t need much (if any) capital to start. You don’t need to rent premises. Hell, you don’t even need a business card.

Thanks to this wonderful thing called The Internet, you can begin right where you are. And whether you choose to sell products, freelance for clients or share your knowledge, there’s a captive audience waiting.

Sure there’s plenty to learn, depending on your chosen path, but that’s the other great thing. You needn’t return to school or stump up for an MBA. There’s a plethora of quality education available online that’ll guide you to whatever you deem nirvana – for you. One of my favourite resources for structured learning is Fizzle. Watch the video on their home page and you'll be convinced.

You need only decide to get in the game and begin your journey. Five years from now, you’ll be five years older, whether you do this or not.

Tomorrow is a brand new day. That’s as good a time as any to begin.

You need only decide to get in the game and begin your journey. Five years from now, you’ll be five years older, whether you do it or not. Click To Tweet

*I'm a big fan of these guys, and I encourage you to check out their sites and social profiles. Gary Vee is huge on Instagram, Medium and YouTube, while James Altucher runs a brilliant podcast and is the author of some very thought-provoking books on business, life and reinvention. Pat is a legend in the online business world and his podcast is consistently one of the top-ranking ones on iTunes. Google them all and learn.


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The Tools I Use and Recommend

Tools and Resources for Solopreneaurs

Books Worth Reading

The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich – by Tim Ferris
Tools of Titans – by Tim Ferris
Jab, Jab, Jab, Right Hook – Gary Vaynerchuk
The $100 Startup – Chris Guillebeau
Choose Yourself – by James Altucher


Thanks for stopping by and I hope we get to hang out more in the future. And in the meantime, please feel free to share your own experiences. You can email me directly at I respond to all emails. If this was beneficial to you, please consider subscribing and sharing with someone you think would also benefit. 

Disclaimer & Disclosure: I'm not a psychologist, and I'm not a financial advisor's elbow. This material doesn't constitute financial advice but rather a collection of personal opinions, based on my own experiences. Some of the links on my site are affiliate links, which means that if you make a purchase, I will earn a small commission. This commission comes at no additional cost to you. I provide links to services or products I have used and liked or researched and recommend. Please do not spend any money on these products unless you believe they will be beneficial to you

Also published on Medium.

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