Making Money from Home: “7 Critical Question Most Forget to Ask Themselves”

Dale Calvert

I have been making money on the side since I was a 4-year-old kid who picked up pop bottles and turned them into our local store for the 2 penny deposit.

My entire adult life I have been an entrepreneur and developed several different multi-million dollar companies and sales and marketing teams. So when I say there are 7 critical questions you need to ask yourself before deciding to make money from home, I sincerely mean it, so don’t gloss over this article, GRAB A NOTEBOOK!

I heard it said one time that the quality of our life is in direct proportion to the quality of questions we ask ourselves and then answer them truthfully. There is a bible verse that says…

“To thy own self be true.”

Understand that my entire adult life I have worked with and consulted people who have gotten the entrepreneur bug. They get excited about making money from home, but quite frankly:





Others jump into the first to make money from home projects they can, rarely understanding what it is going to really take to build a significant income.

They have bought the hype of a self-proclaimed guru online that talks about how easy peezy it all is.

Yes, there are more people creating side-gig incomes than ever before but there are thousands that are sitting on the sidelines, watching, hoping and waiting to “SOMEDAY” be able to do what they see so many others doing.

I am going to be real with you in this article, in hopes that you will be real with yourself; is that fair?

Here is the first brain tweak I hope you will really wrap your mind around.

“Building a side-gig BUSINESS is NOT for everyone, but everyone can make money on the side.”

1. So the First Question Is, “WHY Do You Want to Make Money from Home?”

Some cliché answers like, I would like to have more money, doesn’t everyone want to make money from home, or I have a friend that quit her job selling XYZ products online, so I think that would be cool. These types of answers ARE NOT GOING TO GET IT!

You must know specifically, exactly  W H Y  YOU want to make money from home.

2. How Much Money a Week, a Month, a Year Do You Want to Earn from Home?

This question is very important because it is a key indicator of what kind of business you should start.

Every week, I consult with beginning entrepreneurs that hope to one day quit their job and do their side-gig full time. Unfortunately, I also work with many who have had the dream of earning a side-gig, full-time income for five, ten, fifteen years or longer who have never been able to get over the hump.

Normally because they didn’t clearly define the amount of hard work and personal education it was going to take to be able to build a full-time income with the business model they chose.

So, they have simply gone from the dead-end job hamster wheel to the I am an entrepreneur hamster wheel with very little progress.

3. Do You Have a Clear Understanding of Your Strengths, Disciplines, and Time Management Skills?

Most people start blindly. Just because somebody else has done it, is no guarantee that you can, will, or even should try. No! I am not trying to be Debbie Downer here. There are many disciplined, hard-working people who have entered the entrepreneurial world and failed miserably. Many times because they felt for some reason they were entitled to success, others think they can do it without the focused concentration of developing new skill sets and mindsets, and quite frankly the list of reasons talented people fail goes on and on. Most simply choose the wrong business or quit too soon.

As the great US President Calvin Coolidge said:

I sincerely believe that anyone in today’s world can start and operate a profitable home-based business, IF THEY ARE TRUE TO THEMSELVES, understand their current talents and skills, and understand that they can personally develop most of the skill sets they need to accomplish their reasons for wanting to make money from home.

I would have loved to have been able to dunk a basketball like Michael Jordan, but no matter how much I wanted it, or “believed in myself” it wasn’t going to happen.

I see so many entrepreneurs that think they are going to be the next YouTube Star who have no business being on YouTube. Being in front of a camera is not their strength.

Self-Awareness is a powerful thing that most of the population needs to get a grasp on.

I sincerely believe what one of my personal development mentors Jim Rohn said many years ago.

“Formal education will make you a living, but if you become self-educated you can create a fortune.”

The number one mistake I see first time entrepreneurs make is they approach their make money from home project with a: 

  • Ready
  • Fire
  • Aim


They never really stop and look behind the curtains. They don’t ask themselves enough of the right questions, they just FIRE!  Many times they are down the road several years before they really start asking themselves the question they should have asked BEFORE THEY STARTED!

  • So again, I ask you – WHAT do you REALLY WANT? How much money do you really want to make?

Probably the more important question is, “what makes you think you can accomplish this?”  I mean really?  I am not saying you can’t, but I am saying the world is full of naive people that think being an entrepreneur is easy.

4. What Kind of Business Do You Want to Start and Why?
(What do you want to accomplish over the next 5 years?)

There is a major difference between:

  • Making Money from Home
  • Starting a Side-Gig

Stop for a minute and really think about this. I consult with so many people that are working side-gig businesses they love, but really have no chance of ever scaling up to a full-time income level.

That is cool if their goal wasn’t to ever really quit their job. Are you with me? So one last time, I ask you what do you really want?

I normally ask my clients this question;

If over the next 5 years everything you do working from home works out perfectly, what will your life look like in five years? 

I suggest you ask yourself the same question before you choose your make money from home opportunity.  If you like the answer then you are on the right track

I had a grandmother client last week tell me I will have $10,000 a year in profit, $5,000 for my husband and I to take a nice vacation every year and $5,000 to support my granddaughter with her college expenses.

I have had 25-year-olds tell me, I will be making $80,000 a year so I can escape this corporate rat-race and stop fighting traffic every day.

There is no right or wrong answer to this question. There is only YOUR answer, and to thy own self be true!

5. Who Is Your Business Mentor? Why Them?

Managers learn from professors, entrepreneurs learn from mentors. Mentorship is a lost concept in today’s online tactical world. I first wrote about this way back in 2000 in my best-selling book, “The Success Principle the Internet has Stolen.” The double audio CD set of this book is still available on Amazon.

Hopefully, before you start your make money from home project you have chosen a mentor, and more importantly the right mentor.

Here are some important questions you should ask yourself when choosing a mentor.

  • Have they made most of their money from actually building the business they will be teaching me to build, or selling courses and books?

Don’t misunderstand me, I have invested hundreds of thousands of dollars over my career in courses, books, seminars, and mastermind programs; I BELIEVE IN THEM. IF they are being taught by the right mentors, those who have done what they are teaching you to do; does that make sense?

Let me remind you of the quote I shared earlier.

“Formal Education Will Make You a Living, but if YOU Become SELF – EDUCATED You Can Create a Fortune.”
Jim Rohn

  • I don’t care how many books they have sold, or seminar stages they have spoken on, it is ok to ask them for references of people they have personally mentored and get their contact info, and talk to those people! 

So again I ask, who is your business mentor, and WHY THEM?

6. What Is Your Weekly Schedule for Working on Your Make Money from Home Project Going to Look Like?

When I started my first business from home years ago, before the Internet, I had to decide what I was going to give up, to free up time to start my new business.

At the time, I was a softball warrior, I played in 3 summer leagues. I had to give it up if I ever expected my home business income to go up!  So a question I often ask coaching clients is “What do you need to give up to go up?”

I had a very disciplined schedule. I treated it just like a 2nd job. Monday evenings were team meetings, Tuesday, Thursday and ½ day every Saturday was spent on customer acquisition. Years down the road, I have made millions of dollars, and my schedule is just as disciplined as it ever was because I ENJOY WHAT I DO

It took me 5 long, hard, consistent years to leave my full-time job, but I left and have never looked back. It would have never happened if I hadn’t given up softball and focused on the activities that would move my business forward. I understand that lifestyle business is a big buzzword at the time of this writing, and many self-proclaimed gurus like to talk about building a huge income while you are living your day-to-day life, but the odds of most people pulling that off are very very slim. I would encourage you to have a more solid plan.

Saying you are an entrepreneur on your social media platform, and having a print shop print you up 250 business cards, and attending events where entrepreneurs hang out, DOES NOT MAKE YOU AN ENTREPRENEUR! There is nothing wrong with business cards and seminars, but you must be willing to become self-educated and GRIND to get your business off the ground and profitable.

Today, with the internet, making money from home, or building a real side-gig business is much easier, but I believe you must schedule your time, and STICK TO YOUR COMMITMENT and have a Solid self-education and growth strategy in place.

7. Don’t Think You Can Escape the Grind so Embrace It

We have all heard it said, “If you do what you love, you will never work another day the rest of your life.” I agree with that. However, over the years I have been involved in many businesses that I didn’t necessarily love, but I knew I was in the RIGHT PLACE at the RIGHT TIME.

Timing comes and goes faster than ever in today’s digital world. Over the years I have developed kind of a sixth sense around timing. I have made millions of dollars by being in the right place at the right time, and UNDERSTANDING where I was when I was there. Today, I am involved in a business that I don’t particularly love, but the timing is simply undeniable. I believe I was too smart to let this one pass me by.

To save me some email questions, you can check it out here if you want www.PersonalDNANutrition.com

Even if you are on the right track you will get run over if you just sit there; you must move, you can’t escape the grind.

A business is like an airplane, it uses most of its fuel getting it off the ground, in the beginning. After it is in the air, if you have the right systems in place you can put the plane, and to some degree your business, on auto-pilot. That is why many people seek funding today for their ideas instead of bootstrapping. They want the initial cash to create a quicker launch.

All businesses go through 3 stages

  •  The Grind (The Launch)
  •  The Rise from Momentum
  •  Stability

This has been taught as the “Bell Curve” for many years.

When your business is creating a predictable, ongoing income you have options.  Many people start putting together their exit plans at this point. Some hope to go public, be acquired, or sell their business.

I heard it said years ago, that the only reason to build a business is to sell it. Honestly, I never understood that until years later in my career.

I have some projects like SaveYourBucks.com that are a passion project. I love sharing ideas that will help people save money, make money, and invest their money.

I believe that there will always be a need for some products, services and information.  Most products trend and then decline – we have all seen this happen over and over and the examples are everywhere.

My hope is that in the future, public schools start teaching children about money, investing, compounding interest, etc.

As long as the corporate structure needs workers to get in line when the bell rings, take a break when the bell rings, and conform as everyone has been taught all their lives to do, I really don’t see real financial education being taught anywhere except through websites like SaveYourBucks.com

As I mentioned earlier, over my career I have seen the START STOP most would-be entrepreneurs. I think this has very little to do with the ability to become successful and everything to do with coloring inside the lines as they have been taught as I talk about in great detail in my Programming Your Mind for Success course.

I sincerely hope that you will spend some time, and really think about this article before you start making money from your home project. If you have already started your project it is ok to stop and really ask yourself, “Where am I going to be in 5 years if I keep doing what I am doing today?” Then answer that question, honestly.

If you like what you see with your current plan, then I would ask you, ”Who is your mentor, and why? If that is good for you, my next question would be, “Is your time management and project management house in order?”

If you feel good about all the 7 points above, then learn to love the grind, and I will SEE YOU AT THE TOP!

Dale Calvert is an entrepreneur, best-selling author, public speaker, and one of the owners of SaveYourBucks.com. Join the Save Your Bucks community if you want to stay in the loop regarding live events and exclusive articles Dale will be providing for our members. You can also follow him at www.DaleCalvert.com