Gary Vee Is Wrong — You Shouldn’t Spend Your Twenties Hustling

Tom Stevenson
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When I first started focusing on turning my travel blog into a business that I could live off, one person I looked to for inspiration was Gary Vee.

There’s no other way of saying it, the guy is a phenomenon. I remember watching some of his videos back in 2017 and thinking to myself how does this guy not burn himself out.

One of the videos showed a day in his life and it was just hectic. He was back and forth between meetings, posting content on social media, giving talks in person and running a business at the same time. Perhaps the craziest thing was that he paid someone to film him as he did all of this.

That blew my mind and made me realise how committed Gary was to putting his message out there. It was a message I took on board when I was working in an office job I didn’t enjoy. Now that I’m working for myself, older, and hopefully wiser, I’ve begun to look at his message in a different light.

Arguably Gary Vee’s most famous pronouncement is that you should spend the majority of your twenties hustling and not let up until you’re 30. This suggestion has some merits. If you do that, you’re going to put yourself in a better financial position without a doubt.

It’s this tactic that allowed Gary to become the go-to guy for entrepreneurs who are looking for inspiration. He took his parents wine shop and turned into a million-dollar business, and now runs a variety of other businesses.

It’s an inspiring story, but are his views on hustling right? As someone that spent the majority of their twenties doing the opposite of what he suggested, I’m not so sure.

Travelling, living in different countries and working in a variety of jobs opened my eyes to different aspects of life. I realised how alike we all are, the value of hard work and that there is no one way to do things.

Gary Vee means well, but his advice, and his insistence on hustling, isn’t as helpful as he might think.

You won’t get this time back

Gary Vee’s rationale behind his ‘close your eyes until you’re 30' mantra is that you should spend those years working away so that you can enjoy life more when you’re older. There’s truth in his statement. Your life will certainly be easier if you adopt his approach.

But from my perspective, I’m not sure it’s the best advice. In total, I spent five to six years travelling, living and working abroad during my twenties. Only recently has that involved working on my business and ‘hustling’ as he would put it.

Would I change what I did in my early twenties when I was living in Australia and New Zealand? No. I enjoyed those years, they were some of the best of my life. I learnt a lot about myself, the world and working. I’m not sure I would have been better off devoting myself to working on a business. In fact, I’m sure of it.

The truth is back then, I had no idea what I wanted to do. Travelling was an escape that gave me time to explore new places and figure out what I wanted to do with my life. At around the age of 25 to 26, it clicked into place and I realised I loved writing and developing websites.

Had I not gone travelling, I’m not sure I would have figured that out. I’ve no idea what I would have done instead. The reality is, your twenties are arguably the best years of your life.

Your young, full of life, healthy and minimal worries. It’s the best time to go out into the world and explore. To experiment with different ideas and figure what direction you want to go in life.

Gary Vee’s advice assumes that you already know what you want to do when you turn 20. From my own experience, and many of the people I know, that’s just not the case. Some of my friends still aren’t sure what they want to do today, and they're in their thirties.

Everyone is different, but if you don’t have a firm idea of what you want to do, getting away and travelling for a few months or a year isn’t the worst idea. You’ll always have time to start a business, but you’ll never get your twenties back again.

You should enjoy life and experiment

This point follows on from the one above, your twenties are the best time in your life to live it to the fullest. You’ll have few concerns, your health and a bundle of energy to get out there and see the world.

Among my friends, I’m one of the few that went travelling for a lengthy period. Some of them were sure about what they wanted to do, others were less certain and ended up staying at home instead.

While there is no one correct path, I can’t help but feel you should make the most of your twenties. Spending it slaving away didn’t, and still doesn’t appeal to me.

During the course of my travels, I worked in a variety of jobs. I helped refit an IKEA store, worked as a groundsman at an airport in New Zealand, laid wastewater pipe and taught English. While none of these jobs turned out to be long-term careers they were still beneficial. Even the worst job I’ve ever had, working for two conmen, taught me a lot!

I learnt the value of hard work and diligence while laying pipe. I realised how important planning and organisation is when I taught English, and I learnt the value of teamwork and camaraderie when I worked at IKEA and the airport.

There was no decision behind faking these jobs other than the need to make money. I needed to work and they were the jobs that I got during that time. I realised afterwards that they all taught me something and even if they weren’t the most glamourous of jobs, they all contributed to my outlook on life.

If you know for certain what you want to do as a career when you’re young, then go for it. Honestly, I envy you. I wish I’d known back then what I wanted to do. It took me a few trips, lots of different jobs to realise what I wanted to pursue in life.

Unless you know for certain hat path you want to take, hustling isn’t going to get you anywhere. Taking time to figure things out, on the other hand, will.

Hustling isn’t the answer

Gary Vee is big on hustling. It’s how he got to where he is today and he believes it’s the best way to get to where you want to be. There’s some truth in his message, but it’s missing some nuance.

If you want to start a successful business, become a writer or an entrepreneur, you’re going to have to work your socks off. There’s no doubt about that. What I don’t agree with is his belief that you should hustle as much as you can.

When I started to take my travel blog seriously, I bought into this philosophy 100%. I was obsessed with building the website up to the point where it could sustain me financially. The problem was I became so obsessed with this that I neglected everything else.

All of my waking hours were devoted to improving the blog, writing new content and fixing any issues I came across. I stopped meeting up with friends, if I did, I’d leave early with the excuse of needing to work.

Once or twice, I even said I needed to leave to go and hustle. I cringe thinking about that now. While this work ethic did pay off, it wasn’t without its costs. My mental health took a toll. I was so focused on this singular goal, that everything else was secondary.

I suffered from panic attacks, anxiety, which the lack of social interaction only worsened. It was only when I took a step back and realised that I needed to strike a balance, that I got back on the right path.

Working hard is a prerequisite for success. Gary Vee means well when he says you need to hustle, but if you take his message at face value as I did, you risk ending up miserable down the line.

Instead, it’s better to take another approach.

The middle way

I don’t want this article to come off as bashing Gary Vee. I’m still a fan despite my disagreements with aspects of his philosophy to life. He has a lot of valuable insights into the world of business and life. But his characterisation of your twenties as hustling years is something I don’t agree with.

For me, his approach is too much. I couldn’t sacrifice the best years of my life to build a business that may or may not succeed. You’ll never get this time back. Sure, if you’re successful, you’ll free up more time later on, but I believe you can achieve what Gary suggests without all the sacrifice.

I believe that there is a middle way you can adopt. Take Gary’s advice on board. Work your socks off and develop your ideas, but don’t dive into the deep end.

Instead, walk the line between hustling and enjoying your twenties. Take time to explore the world, experiment with ideas that you’ve always been interested in and work in different environments to get a better perspective on life.

The truth is, you can take Gary Vee’s advice and implement it without going the whole hog and quarantining yourself in your room until you’ve made it. It’s not one or the other, you can do both.

Don’t waste your twenties stuck at home hustling 24/7 when you can get out into the world, meet new people and see new places, while still accomplishing your goals.

The hustle never stops, but it shouldn’t stop you from living.

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