What to Do When Your Hustle Isn’t Working

the truth about hustle“Rise and Grind” is something we’re all used to hearing, seeing, and believing these days. In order to get what you want in life -in order to get ahead- you have to get up early and grind yourself, your gears, and your ambition against the motion of the day.

Well, technically it’s the idea that you should attack the day as soon as you wake up, and stay focused as you get into the groove of the daily grind of work and responsibilities. Essentially, you have to hustle if you want to make things happen.

Sometimes the hustle can bring great success and confidence, and other times the hustle brings exhaustion, despair, and defeat. So what’s the catch with hustle?

In this episode of the podcast, we’re exploring the tale of two entrepreneurs and the differences between a hustle that works and a hustle that hurts. No, it may not cause physical harm, but a hustle that doesn’t work is every bit as exhausting and fruitless as trying to ride a bicycle through wet cement.

Let’s fix that and get you on your way. You do NOT need to grind in order to be successful. You just need to recalibrate your hustle. Take a listen and let me know what you think in the comments below. [Subscribe Here]


One of the main reasons people venture out on their own and leave the comfort of the cubicle-lined nest of Corporate America is the burning desire to be your own boss. Unfortunately, too few realize that being the boss means doing the work of the boss, and the managers, and the crew, and the salespeople, and the marketing team and the– you get the idea.

When a client of mine (whose permission I have to sharing this story as long as I hanged his name), who we’ll call Evan saw the bright light of entrepreneurial came at the end of a very dark desk-job tunnel, he leapt into action.

Evan was working middle management in middle America, as a project production manager for a property management conglomerate. He had a corner cubicle with windows and plenty of space – it was the best corner office he was ever going to get.

He ran reports of the properties in the region, what his sales and development staff were up to, and coordinated the projects in business casual from his corner cubicle in Louisville, Kentucky. Life was pretty sweet. He and his wife were about to celebrate their second anniversary, and she had just announced her pregnancy. Things were progressing along nicely, right?

He went out with a few friends for a day of golf, and ran into a former coworker who had ventured out on his own. Mark (the former coworker) left their company to pursue his own passions in the business world and was having a great time being independently successful.

the truth about hustle

A week later, Mark called to get everyone together for another round on his dime, but Evan had to decline because he had too many projects at work. He felt the draw to start his own company right from that moment. The feelings only grew from there. Every time Mark could do whatever he wanted without answering to a boss, Evan grew more disillusioned with his career path.

Eventually, Evan could take no more and launched his own company. He knew enough to be dangerous in property management, so he left his job and started his own property management firm. He was waking up and hustling as hard as he could. He was calling properties and and owners to bid for management contracts. He was visiting businesses. He was sending hundreds of emails each week.

He landed a few small properties quickly with his approach. Things looked good. He was controlling the entire situation and it was working. Sure, he was working from 6am to midnight 7 days a week, but he was his own boss!

Evan lived the “rise and grind” mantra every single day. He couldn’t go to social gatherings because he was hustling. He couldn’t celebrate moments and occasions with his wife because he was hustling. He was growing his business and his clientele, because his hustle was effective.

He was busy! He was important. He was disconnected from his wife. He was distant. He was exhausted. He was miserable.

He was motivated by not falling on his face. His fear of not having enough had him chasing opportunities around every corner. He wanted freedom to choose in his life, but he never got it. He traded one role for 10 more. He pursued wealth and business success, but had no desire for the work he was doing. His hustle was effective, but his hustle hurt.

On the flip side, one of my favorite stories is that of Brian Chesky and Joe Gebbia. They were both designers looking to make ends meet in San Francisco and at the very least, get some help paying the rent on their apartment.

They had a little extra space and liked people, so they put their extra loft space up for temporary rent – for the weekend or a day or two at a time. The biggest thing they knew they could offer was cheap accommodations and home-cooked breakfast with a smile.

You essentially got an air bed and breakfast. When it turned out to be a hit, they discovered other people looking to bring a service like theirs to other cities. That’s when the real hustle began.

the truth about hustleBeing designers (and living in San Francisco), they took liberties with cereal boxes and designed a new box for each of the Presidential candidates and launched them at the Democratic National Convention later that year – Obama-O’s and Cap’n McCain Crunch, respectively.

Selling each of these as promotional Presidential memorabilia allowed them to raise $30k and take their concept to phase 2. After that, they started pitching other investors to help them build a searchable website for different locations across the country.

After pitching investors, continuing to hustle for more funds to build their service, and putting in the long hours, they were exhausted. But they’re not interested in stopping because they’re not burned out.

Fast forward a few years, and they’re still hustling. They fly, with their teams, to cities all over the world to help others follow their brand standards. They have launched new initiatives to train the public on how to successfully use their service, and they don’t need funding anymore.

Because they believed their service and idea was simple, attractive, and fulfilled a need in both themselves and their customer (help people travel and stay places with a personal touch at a better price), their hustle helped.

Their Airbed and Breakfast (AirBnB) is now in cities all over the world and valued at $31 BILLION.

What’s the Point?

There are few things that have as large an influence on your prosperity as your attitude about what you do, and more importantly, why you’re doing it. Anyone can get rich in America, but far too few are getting rich doing what they love.

They may earn a lot of money, but they’re working for the weekend – for the chance to escape and live the free life of Saturday and Sunday.

The hustle has no schedule. It knows no weekends. It knows no start and finish time. You, my friend, have to set the boundaries and reasons for using it.

When I was working on purchasing Jami’s engagement ring, I was hustling while she was off at work by doing things I didn’t want to do, but I knew WHY I was doing them. I was working on cars in driveways for months in secret. I was doing light electrical work around town. I was hustling to raise money off the books, and I was working as often as I could because I had a goal.

the truth about hustleHustle has no emotional attachment to what you are trying to accomplish. Think of it like gasoline. It doesn’t care if you’re using it to run a generator to power a house after a devastating natural disaster, or as an accelerant to to burn a house down.

You can hustle without burning out and without compromising your integrity, but you can just as easily hustle and “grind” yourself into overworked unhappiness. So if your hustle isn’t working to bring you what you truly want, I invite you to pause and take a look at what you’re using it for.

You might be trying to accomplish tasks and goals for something you don’t truly want, so you’re subconsciously hoping it doesn’t work so you can escape. You might also be looking for it to fail so you can be right and say, “I told you so- to yourself or someone else.

You might also be struggling because you’re stubborn and don’t know what you’re doing, but refuse to stop and ask for directions. Seriously, ask for help. Ask for guidance. Ask for clarity.

If your hustle isn’t working it’s usually because you’re not truly interested in the goal you’re pursuing, or you have no idea what you’re doing and refuse to ask for help.

Make “reflecting and adjusting course” part of your hustle, and you’ll get there. I promise. And if you realize the goal you’re working toward isn’t really what you want, quit.

Sometimes the best hustle isn’t the one that makes you rich, it’s the one that helps you see that what you’re doing is making you poor – financially, emotionally, spiritually.

Get clear and go forth, my friend.

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The Author

Blake Hammerton

Blake Hammerton

Blake Hammerton is the founder and coach at The Sharp Gentleman, and helps men earn more respect while gaining confidence in who they are. He is a certified relationship coach and loves writing about men's fashion, style, character-building, relationships, travel, adventure, and more.