Ready to Leave Your Job and Start Your Own Business?

Ready to leave the 8 to 5 daily grind? Here are a few thoughts to help you make the transition.






A couple of generations ago, the dominant career philosophy was one job for life. You choose a company to work for, put in your thirty years, and retired with a pension or some other form of employer-funded investment designed to provide income for the rest of your life.

It’s a far cry from today’s worker who is constantly on the lookout for new opportunities  – at least she should be. Changing employers every few years can be one of the best ways to move up in professional status, income, responsibility, and authority –especially early in your career, because no one is going to be a better curator of your career than you are.

But if you’re at that point where you’re thinking that you’re next career move is to leave the life of an employee and start your own business, the process of evaluation becomes even more critical.

But being receptive to entrepreneurial opportunities doesn’t mean jumping at the first shiny new thing that comes along. Successfully moving from employee to entrepreneur is usually the result of a combination of things, including street smarts, timing, and knowing how to negotiate, to get what you want. And that’s the big assumption here—is that you know what you want.

Conversely, It also means knowing what you don’t want.

Being unsure or deciding to move forward just because you’re ready for a change can be financially devastating. Regardless of what form your new business takes, you’re making an investment in your professional future, and you want to make sure that future is going to be a long one.

It’s a big transition to go from an employee to being completely in charge of your own financial destiny. Make the wrong choice, at the wrong time, and you’ve not only lost your job and the income it provides, you can jepordise your savings, the equity you have in your home, your professional reputation, and here’s the hard one – you can even put your most cherished personal relationships at risk.

So anytime you’re considering a move to strike out on your own, there’s a lot of foundational criteria to think about, especially what you hope to gain in the short and long term. That’s why Jumping ship to follow the promise of big money may not be the right reason or motivation for you to make the move, especially if you have to compromise your professional ethics or move away from your ultimate career goal.

So, how do you know when leaving your current employer to start YOUR OWN BUSINESS IS THE RIGHT MOVE TO make?

 Hey, welcome back. This is Roger Reid with another episode of Success Point 360.

Like any decision that can potentially affect your income and how you spend your time, you’ll probably make ongoing comparisons with others who are doing something similar and measure their situation in terms of compensation, career advancement opportunities, industry recognition, and job satisfaction against your own.

And as long as you don’t fall prey to the grass if always greener syndrome, those kinds of comparisons can be very useful.

The first comparison we make? It’s usually money.

Let’s say you want to leave your current employer and start an online business.

So you research the average income for the niche market you’re planning to serve. It is enough to replace your current paycheck? And most important, can you grow it with greater effort or more effective marketing?

For example, if you want to make $250K a year and your career goal is to become a podcaster. But the average income for a podcaster during the first year or two is seldom enough to pay for equipment and hosting, and unless you have another source of income that’s going to offset the deficit, then it’s probably wise to consider another way of making a living. Certainly, podcasting can be a part of your business marketing plan. But as a stand-alone business, very few podcasters make enough money to pursue the activity as a core income generator.

And what about your investment of time?

Are those who are generating an enviable income devoting a reasonable amount of time for the return they’re receiving? Or are they working 7 days a week, 12 hours a day? And if that’s the case, are you willing to do the same?

I want to take just a moment to talk about the difference between passion and professional success. This is especially important if you know you’ve had it with being an employee, but you’re still trying to decide what kind of business would be right for you.

I’ve heard many business gurus, bloggers and podcasters claim that financial success is found at the intersection of passion and talent. In practice, that means making a list of those things that get you excited — the activities that motivate you to the point that you’re willing to get up every morning and do them again, day after day. When you’ve identified those, then make a second list of your talents and expertise. When you find a match between the two lists, that’s your passion — what you should pursue as your occupation.

If you’ve done the exercise, you know the results are usually nothing more than a projected fantasy. You can’t trust the outcome — you can’t know for sure — because you haven’t tried it.

Here’s the truth: We find our passion by trying out new and different things.

We may be terrified of public speaking, but after forcing yourself into making that training presentation at work or giving the best mans’ speech at your friend’s wedding, you find out you really enjoy holding the attention of the audience while you tell a story, teach, or entertain.

Most people discover their passion by doing the work and then becoming passionate about it — because they enjoy it, or it brings them a sense of accomplishment, or they can make money at it.

Discovering your passion comes from doing, not dreaming.

So when it’s time to consider what you want to do next — especially when it’s another way of making a living — don’t spend your time looking for some magic correlation between your interests and talents. Instead, think about new things you can try, new activities in which to participate.

Need more information?

The process of research can often lead you to a new career because of what you don’t find.

If an internet search brings up sources that are missing the details you need, or you don’t think they represent the current state of the industry or market, consider starting a website and provide the content you believe is important for others to know.

Teaching others how to create desired results or change is a great way to develop a curriculum that can be sold online. If you have some level of expertise in a particular subject, write about it. Submit your articles to online publications or post them to your website.

You can also create videos or podcasts that will help establish yourself as an online expert. And if the market is there, you can offer educational products for sale in the form of books or training courses.

Just keep in mind that when creating an online business, you have to put the emphasis on providing value for the consumer.

The fact that you use the internet to market your product or service doesn’t alleviate the responsibility of making a clear and concise presentation, building trust, eliminating risk, streamlining the process of purchasing, and delivering your product within a timeframe that meets the customer’s expectations.

And don’t be coaxed into thinking that building an internet business automatically gives you license to lower the market’s objective standards of quality. Hiding behind a landing page doesn’t grant you the privilege of trying to hawk a piece of worthless junk or a well-worn piece of information that has no real value.

If you don’t feel comfortable with the idea of sitting down with a prospective customer face-to-face and making the same presentation you plan to put online — including the feature-benefit story, the testimonials, the price and guarantee — then why would you offer it via a website?

Make a commitment to stand behind whatever you’re selling.

If a buyer has a problem or a question, make it clear you’re there to help. And if the product doesn’t meet their expectations — for any reason — you’ll gladly refund their money.

Certainly, use the internet as a tool. But build your business on the same traditional concepts that have made small business owners successful — with or without the internet.

While you’re in the process of considering new options, try asking yourselves these questions:

Will your new business lead you to your life’s work? Or is it simply a way out — a feasible alternative to a job you hate and need to leave?

Are you looking for meaning in your work or just the promise of more money and financial independence? One doesn’t necessarily lead to the other.

How long do you see yourself doing this type of work? Are you ready to commit to a new profession for five years? It takes time to build brand recognition and a reputation for quality. If you’re not prepared to make the commitment, it’s the wrong choice.

Any new plan to acquire or build a new business should also include an exit strategy.

How will you separate yourself from the business when it’s time to move on? If you plan to sell it, keep in mind that some businesses can be evaluated based on their net cash flow, brand recognition, customer base, or the cash value of assets. Others are valuable because of the individual running them.

If you plan to build value through celebrity status, you’re not building a business, you’re creating a personal brand. If your goal is to build a business that can be sold in the future, design systems and processes that can be replicated by others.

Finally, don’t eliminate a business opportunity simply because it’s not internet-based.

Yes, the idea of creating an automated money machine feeding your bank account 24 hours a day is appealing. But many of these so-called “lazy ways to riches” are often nothing more than click-bait.

Typically offered as an online business program, you’re promised the “inside secrets” to acquiring wealth and influence. What you end up with is a blueprint to create a duplicate copy of the same business — including the identical pre-packaged insider secrets, landing pages, and advertising copy. Little more than a digital version of a Ponzi scheme, these programs waste your money and time.

Whether you decide to work as an employee or follow the path of the self-employed, the success you ultimately achieve will reflect your commitment to do the work. There are no shortcuts or “easy ways to riches.” (At least, I haven’t found them.)

I want to address a question I’ve received from several listeners about the interview with Jaye Frances. At the end of season three, I promised a special episode in which I would sit down with Jaye and discuss the current state of the writing industry, especially as it pertains to new writers just starting out in the business. Due to a scheduling conflict, that episode had to be rescheduled. It’s still happening, and I plan to have it in production in the next few weeks. And because I know there’s a lot of listeners who are looking forward to hearing what Jaye has to say, I’ll be posting an update on the website as soon as I have a firm release date. I appreciate your patience and I promise, it will be worth the wait.

Hey, that’s it for this episode. If you have questions or comments about anything we’ve talked about on the podcast, please use the voicemail tab on the website, or you can send me an email, at

Thanks for listening, and I’ll see you next time.

© 2021, Roger A. Reid

 For more information about the author, his work, or to subscribe to this podcast, visit

Be sure and check out my new book now available on Amazon in eBook. It’s titled Better Mondays: The New Rules for Creating Financial Success and Personal Freedom (While Working For the Man)

I’ve lowered the price for the Kindle version, so if you or someone you know is struggling with a job that doesn’t provide anything more than a paycheck, or you’re ready to use your employer as a launching pad to start your own business, you’ll find the tools you need to take control of your professional success and to change your life for the better.

You can find more information on my website, I’ve posted the first chapter on the site as a free read, so I encourage you to take a look.