Tag: Sylvester Stallone

The 10 Essential Questions Every Entrepreneur/Artist/Coach/Side Hustler Needs Answered

by Joe Barnes


Pratical Tools & Tips


Date: Dec 20, 2021

The 10 Essential Questions Every Entrepreneur/Artist/Coach/Side Hustler Needs Answered

According to The Washington Post, 4.2 million people quit their jobs in October 2021.

‘The Great Resignation’ is here.

People are no longer prepared to accept excessive working hours, broken promises and working for nothing more than their companies’ profits and a pay check at the end of each month. Instead, they’re becoming aware that the internet is making it easier to be an entrepreneur, artist, coach or make a living with a combination of side hustles. 

You may feel the same way.

Furthermore, you might have been feeling this way for a long time. However, now ‘The Great Resignation’ has legitimised your desire, you’re ready to get started on this exciting journey. 

As with every change, it’ll feel daunting. You’ll be uncertain about both yourself and the industry you’re moving into. 

With this in mind, read the answers to the following 10 questions. They’ll tell you all you need to know about the entrepreneurial, artistic, coaching and side hustle experience. 


Question 1: Should I work off inspiration or stick to a schedule?  

Older readers might be familiar with Sylvester Stallone’s story of creating the original Rocky movie. After years spent struggling as an actor, he turned his hand to writing after being inspired by the spirited effort Chuck Wepner put forth in his defeat to then heavyweight champion of the world, Muhammad Ali. Still buzzing from the fight, it took Stallone only three and half days of writing to create the first Rocky script.

So, inspiration is powerful. Use it for ideas and to get you started. However, understand that routine, a smart schedule and the ability to be consistent, day in day out, is the only way to achieve long-term success.  

In his ground-breaking business book, The ONE Thing, Gary Keller explains that the key to success in any project is laser like focus. To develop this, he suggests you split your day into 4 hour ‘time blocks’. 

Ask yourself, ‘what’s the most important part of my most important project?’

When you have your answer, spend 4 hours every morning (if you work another job during the week, use the weekend) doing this work. Other work related to this project can then be completed in the afternoon or evening but give your most productive hours of the day to your most important goal. 


Question 2: How many hours a week should I work on my project?

In an ideal world, you’ll complete five ‘time blocks’ a week.

These will be performed Monday to Friday and you’ll then do less important work in the afternoon or evening. 

This ensures you work a minimum of 20 hours a week on your entrepreneurial, artistic, coaching or side hustle business. Of course, this is a minimum and, if you have more time available, you might put in another 20 or 30 hours. 

But what if you don’t? What if you have to support yourself with an employed role?

If this is the case then the weekend provides an ideal time to complete two ‘time blocks’. In addition, during the week, you might spend a further 4 hours working on less important tasks (giving you a total of 12 hours a week). 

Whatever the case, you must work consistently, for at least 10 hours a week (but preferably more) to build the momentum needed to be successful. 


Question 3: Do I need a mentor?

In 2007, I found a writing mentor. He helped me improve my writing, refine the concept for my first book (changing it from a generic self-help manuscript called, How to Live your Dreams, to something with an edge) and provided the positive feedback needed for me to believe in myself. 

This transformed my writing and saved me years of trial and error. However, such a successful mentoring partnership isn’t always easy to find.  

Some mentors or coaches require thousands, if not tens of thousands, of dollars for you to work with them. They promise the world, talk about their CEO clients and all but guarantee success. 

Be wary of such people. No mentor, irrespective of how much hype surrounds them, knows the secret to success. 

So, if you feel uncertain about a potential mentor, or uncomfortable about parting with so much cash, then trust your gut and go it alone for the time being. 


Question 4: How much money do I need to support myself?

Less than you think. 

Most of the privation you’ll experience on your entrepreneurial, artist, coaching or side hustle journey will be psychological. Your lifestyle might have to change but your livelihood won’t be threatened. 

Ideally, you’ll have enough money saved up to support yourself for at least a year. If you haven’t, there are some side hustles you can start working that’ll provide you with an immediate income. 

Either way, it’s likely you’ll have to make cut backs. Instead of going to the gym, work out at home. Instead of taking three vacations a year, have only one and don’t travel abroad. Cut back on the amount you spend on food, restricting take outs and dining out.  


Question 5: Is there a secret to success?

No, so stop looking!

Despite what an overpriced course or business coach is going to tell you, there is no one strategy, tactic or approach that’s going to work all of the time. Furthermore, there isn’t some secret information, that only the top guys and girls in your industry know, that once you discover, will ensure your success. 

Instead, work consistently on your business almost every day. 

Form partnerships with people in your industry. 

Do your best to understand current trends and provide your customers or clients with a product or service they want. 

And, above all, believe in yourself, what you’re doing and what you’re creating. 


Question 6: At some point, should I consider giving up? 

Undoubtedly, the quest to become a successful entrepreneur, artist, coach or side hustler is incredibly difficult and one of the hardest challenges you’ll undertake. As a result, there’ll be numerous moments when you’re faced with situations that appear to demand more than you think you possess.

In such moments, the immediate temptation will be to look for the easy way out and bring an end to the psychological or physical pain you’re experiencing. When this occurs, you must train your mind to dig deeper and resist.

Then, ask yourself these questions and use the answers to get back in the game. 

Who do I know in my industry, but haven’t yet approached, who might be able to help?

What new business ideas do I feel really excited about but haven’t yet developed? 

What’s one thing I’m scared of doing which I know will have an impact?

Is there some way I can improve my skill-set?

Only if your mind draws a blank on all of these questions, or you have a more inspiring opportunity you want to take, can you consider giving up. 


Question 7: How long is it going to take to be successful? 

Longer than you think. 

It took me four and half years of part-time work to write and release my first book (I thought I’d complete it in 6 months). We tend to overestimate how quickly we can get things done. Therefore, don’t ask yourself how long it’s going to take, ask yourself the following two questions instead.

  1. Am I enjoying what I’m doing?
  2. Am I making progress?

If you can answer yes to both then keep going. You’re on the right track. 


Question 8: Should I do it all by myself or should I ask for help? 

Make no mistake, you will have to be the driving force behind your business. 

That being said, avoid the mistake of thinking you don’t need any help.

Building partnerships with other authors has been the most effective strategy in helping me reach a wider audience. 

  • I’ve gained almost two-thirds of my entire email list from collaborating with other authors on joint book promotions. 
  • I’ve gained almost one-third of my book sales through partnering with a publishing company on the release of my second book and having author friends, like Thibaut Meurisse, promote my books to their email list. 

Build these partnerships by being genuine (don’t be a kiss ass) and having something of value to offer your potential partner. 


Question 9: When is the right time to quit my day job? 

Back in November of 2013, I took a 4-month sabbatical from my tennis coaching and hypnotherapy business in the hope that, in this short space of time, I could make a such a success from my writing that it would become my full-time occupation. 

It didn’t. In fact, I only made a couple of hundred pounds. I was missing the foundations that would have enabled me to successfully make the leap. 

Before you quit your job, make sure you’re earning a minimum viable income (the absolute minimum you need to survive) from your new business, artistic work, coaching or side hustle. 

If you haven’t reached that level yet, then keep working your day job, or slowly reduce your hours (or go part-time) as you build your additional income.


Question 10: Am I crazy?

Absolutely not!! 

It’s very easy to doubt your sanity when you’re going against the grain and following a different path to your peers and parents. There’ll be moments when you look back at the security of your former life and wonder what the hell you’ve done. 

When this happens, ignore your doubts. 

Your future success will validate your decision.

Until then, remind yourself that humanity needs its game changers, risk takers and innovators. You are part of a small group that prevent the stagnation and suffering that ensues from always following the status quo. 

(To watch a video version of this blog post, where I answer these questions in person, click here)


If you want to discover a passion you can make a living from and overcome the fears that are holding you back, check out my free course 30 Days to Escape The SystemClick here to get the course right now! (You will find the unconventional approach to developing belief and self-confidence fascinating!) 

(image taken from CollegeDegrees360 photostream on flickr.com)