Working from Home Isn’t What You Think: 3 Steps to Finding Success

I’d like to let you in on a little secret—working from home is fantastic, and I’d be lying if I said that it wasn’t immensely rewarding. However, the reality is that it takes hard work and determination in order to succeed. Because of this, if you’re seriously thinking about transitioning into a work at home position or a home-based business, it can seem overwhelming at first; almost like a mountain that can’t be scaled.

But at HighYa, we’re passionate about helping you become more informed, whether it’s about your recent “As Seen on TV” purchase, or about earning money from the comfort of your own home. As such, while we covered the basics of working from home in our first installment in the series, in this episode we’ll focus on the nitty-gritty of making your work at home dreams a reality.

But before we dive in, let me share with you how I found myself working from home, and the path that led me there.

My Journey to Working from Home

My father grew up in a generation that valued working hard in order to achieve financial success. In fact, family life often took a back seat to whatever the needs of the employer were, as his generation thought that providing increasing levels of financial support for their families was precisely what was expected of them.

Because of this, my dad got up very early each morning, spent a minimum of an hour driving in to the office, worked 14 or 15-hour days, five to six days per week, and then spent an hour or two driving back home. Because of this, several days would often pass during the week where I didn’t see him, and when I did, it was understood that he wasn’t to be disturbed.

The End of an Era

Although my dad’s years of hard work allowed my mom and I to live a comfortable life, it ultimately caught up with him, and in 2012 at the age of 64, he was diagnosed with lung cancer. By the time it was identified, the cancer had already spread to all of his major organs, and he passed away just over a month after his diagnosis. In a cruel twist of fate, he suffered a stroke soon afterward, which left him with only a minimal ability to speak.

There were so many things I wanted to ask him in his final days; so many insights that I wanted to learn. But somewhere near the top of the list, I wanted to know if he felt that all the time he spent at work was really worth it. In other words, did he look back on those long days and nights with regret, or did he feel that his immense sacrifices were worth the extra money?

A Shift in Perspective

Few things can impact the direction of our lives quite like the passing of a loved one can. And to me, one thing was crystal clear: I remember how it felt not having my father around throughout much of my childhood, and I wanted my girls to look back on theirs with a completely different perspective.

Up until this point, I had been working in the insurance industry for the better part of a decade, and while I enjoyed the people I worked with, I quickly understood that most large corporations place their employees at the bottom of their “Things to Care About” list. I watched as good people who worked at their jobs for 30 or 40 years got laid off less than six months before their retirement. I heard so many promises about this and that over the years, almost none of which ever materialized. And I sat idly by as the company demanded more and more of its employees, without giving anything in return. I knew I needed to get out, and although I didn’t know how to proceed, I learned two important lessons from my father’s passing:

  1. I wanted to earn decent money doing something I was passionate about.
  2. I didn’t want to waste one precious second of my children’s childhoods on helping to make someone else rich.

From Past to Present

Once I grounded myself in the reality that I wanted to enjoy my work and to give my children as much of my time as I possibly could, I decided that there’s no time like the present. I was motivated to live my dream, so I got to work achieving it.

I had always enjoyed writing and I knew that I could earn money remotely by doing it (more about this later), so I asked friends and family members who owned businesses if I could write some copy for them, and I slowly built a decent portfolio that I could put in front of potential clients.

After building a few key pieces and landing a few freelance assignments, I began working nights and weekends “in the trenches,” often for long hours and low pay, just to get some experience under my belt and work out the kinks. Months later, after numerous conversations with my wife, I decided the time was right, and I put in my 2-week notice at my job.

And frankly, I was terrified. I felt like I was jumping off a cliff with only a napkin as a parachute, and I constantly second-guessed myself. What if I failed? What if I couldn’t bring in enough money? What would my friends and family members think about my decision? In the end though, I knew I had what it took to succeed, and I understood that I would just have to put my head down, weather the ups and downs, and keep my eye on the prize.

Why am I Telling You All of This?

In the end, this isn’t intended to be a Debbie Downer story. Instead, it’s all about understanding what you want in life and achieving your “big” goals, despite the obstacles you’ll experience (and you will) along the way. And perhaps most importantly, it’s about discovering who you are and what you’re made of.

Today, I’m fortunate to have been a successful freelancer for well over 2 years, which is pretty amazing considering the fact that I began this journey without a single client and had no idea what the immediate future would hold.

With this said, I understand that your reasons for wanting to work from home may not be the same as mine, and that you may not be comfortable with “jumping off a cliff.” Whatever position you currently find yourself in though, I want to help you realize your dream by working smarter, not harder. After all, there’s a lot of good, usable information about working from home out there, but it’s often targeted at those who already have a good idea where they’re headed. Instead, if you’re starting from square one, this installment of our work at home series is focused on getting your career off the ground. After all, how can you get where you’re going if you don’t know where to start?

With this said, here are three steps that can solidly put you on the path to working from home.

Step 1: Employee or Entrepreneur?

You might recall that we briefly discussed four basic work at home opportunities in our previous Work at Home article, two of which were becoming an employee for an existing company or starting your own, while the other two involved direct and affiliate marketing opportunities. You might also recall that we mentioned staying away from the latter, since those industries are rife with scams and often entail steep learning curves and years of experience in order to be able to replace your current level of income.

As a result, we’ll take this opportunity to reiterate that your best chances for success as a “work-at-homer” are either for an existing employer, or by starting your own business using skills you currently possess. As such, let’s take a look at each of these options in greater detail than we did last week.

Working for Someone Else

As we noted in our previous article, finding a company that allows you to telecommute is often the best way to transition from a typical office environment to working from home. After all, existing companies have already put in all the hard work, from setting up their businesses to attracting clients and hiring employees. In other words, you simply get hired, learn the ropes, and enjoy working from the comfort of your home. On top of this, being a work at home employee also can provide you with a steady paycheck, a set schedule, and the comfort of generally knowing what your day will bring. You’ll also typically have important benefits such as health insurance and paid time off for sick days and vacation.

However, keep in mind that being a work at home employee also has its downfalls. You’re still working for someone else, so you may not be able to control your future as much as you’d like, and you’ll often have to go into the office (if local) for meetings and such. As Yahoo’s remote employees learned over a year ago, some companies have begun reintroducing them into traditional offices, so it’s important to keep in mind that your work at home status is never assured.

Also, even though you’ll be at home, you’ll still need to work a set schedule, which may not give you the flexibility you were searching for when deciding to work from home in the first place. Finally, you may not be able to pick and choose between work at home opportunities you’re passionate about, and those that are just ho-hum. This is because most entry-level work at home jobs are service-based; e.g. translator, virtual assistant, tech support, or customer service representative, for example. As such, unless you’re legitimately passionate about these types of jobs, you might experience the same discontentment as your previous position, but now you have the opportunity to be “job-restless” in your home.

With this said, if you’re looking to connect with a company who’s hiring work at home employees, websites such as,, and can be great resources. Also, from a corporate perspective, this 2014 Forbes article outlines the top 100 companies offering work at home jobs. We’d also strongly recommend reading The 4-Hour Workweek by Timothy Ferriss and Remote: Office Not Required by Jason Fried, both of which will give you tons of actionable advice that will help you along the way, from convincing your current employer to let you work from home to setting up your workflow system.

On the other hand, what if you’re not interested in working for “the man?” What if you want to set out on your own and blaze new trails? If this sounds intriguing, you may want to consider becoming your own boss.

Working for Yourself

When compared to working for someone else, becoming your own boss can be simultaneously thrilling and downright scary. After all, when you’re the boss, the sky’s the limit—but should you crash and burn, you’ve got no one to blame but yourself.

The good news is that when you decide to start your own work at home business, you can make the transition as fast or as slow as you’re comfortable with. In fact, since this is your first foray into business ownership, it’s probably a good idea to start our working part time, including nights and weekends. After all, it’s almost always a good idea to figure out most of the basics before quitting your current job.

Sure, it can be tiring and it’s definitely not “sexy” like some rags-to-riches movie, but it’ll be extremely rewarding in the end, and it can dramatically increase your chances for success. This is because having a steady source of income (or at least some significant savings) and reducing your debt as much as possible can give your business the buoyancy it needs during your first critical few months. Otherwise, the stress of starting a business along with the stress of paying bills can cause you to throw in the towel way too early.

Also, an important tip is to regularly work on your business as often as you can. Even if it only involves an hour per day, 3-5 days per week, you can make some serious headway in just a few months’ time. If you find yourself overwhelmed at some point, identify the most important thing you need to accomplish in order to move closer to your dream, and then work only on that thing. Then, once you’ve accomplished it, identify another key aspect and keep working on it until it’s been achieved.

Step 2: What’s Your Business All About?

While making the commitment to work from home is a big first step, deciding what you’re going to do for income is definitely the most important. Why? Because you’re going to experience a rollercoaster of emotion during the initial stages of your business, and only by truly enjoying what you do will you be able to weather the peaks and valleys.

With this said, if you’re looking to work from home as quickly and inexpensively as possible, the best way to start bringing in the dough is by making “you” your business. In other words, you’ll pull from your existing skillset to start a service-based business. But instead of being an employee, you’ll be able to make your own hours (for the most part), spend time with your family, and go in whatever direction you see fit. In addition, you’ll only need a computer, a scanner/printer, and an internet connection, all of which you probably already own.

So, what’ll it be? Do you have a knack for writing? Think about becoming a copywriter, editor, or proofreader. Do you enjoy art? Try a career as a freelance illustrator. Do you have a history in accounting, or are you great at multitasking? Perhaps you could start an accounts receivable or a remote assistant business. If you’re having trouble finding your niche, LifeHacker offers 4 great tips for figuring out what you really want to do. From there, you can decide whether or not you want your business to be broad or specialized.

With this in mind, if you don’t have a clue where to start, reading books and finding a mentor are key activities that can ultimately mean the difference between success and failure. If you have a friend or family member who’s successfully working from home, reach out to them and ask for some pointers. You’ll be surprised that most people who’ve experienced any form of success are more than eager to help others do the same. However, once you ask for their advice, be prepared to put it to use and to work hard while doing it.

Step 3: Putting Things in Motion

In the past, starting a solo business often meant that you had to bump along and make a ton of mistakes in the process, hoping that you don’t do anything stupid enough that leaves you in financial ruin. Today however, the internet offers hundreds or thousands of resources that you can access in seconds, giving you an unprecedented amount of information at your fingertips.

This isn’t to say that you won’t make mistakes though, because you will. Lots of them. But remember to ask for help when you hit a bump in the road, because  someone has almost certainly been where you are, and can offer some useful insight to help you get through it unscathed.

With this said, where you’ll turn depends largely on the niche you’ve decided to enter. However, for a wide range of specializations, freelancing websites like Upwork (formerly oDesk), Elance, and Freelancer can be invaluable resources when you’re just starting out and are looking to build a reputation.

But you’ll pay for this convenience. How? While the biggest benefit is that these sites can give you immediate access to hundreds of gigs specifically related to your specialization—from administrative support to web development and everything in between—they’re often awarded to the lowest bidder, especially if you haven’t yet built a reputation on the website. For a great reference on how to start your freelance career without prior experience, Mashable has a must-read article.

Bottom Line: If You Want to Work from Home, there Are No Shortcuts

So, where does this all leave you? Here’s the short and sweet version: If you’re looking to work from home, you have to put in the time and effort to make it happen.

There’s definitely never been a better time to make the leap, but it’s not always an easy process, and it’s definitely not going to happen overnight. And to put it bluntly, if you think by paying $50 for some random work at home website that you’ll begin cashing huge checks in days or weeks, it’s just not going to happen. The sooner you realize this, the closer you’ll be to achieving your dreams.

Sure, there are plenty of people who will promise you the world and are happy to take your money while doing it, but at the end of the day, these “opportunities” are not what you’re looking for if you want to create a long-term work at home opportunity.

With this in mind, be sure to stay tuned for next week’s article, where we’ll explore some of the most common scams within the work at home industry.

Derek Lakin

With more than a decade of experience as a copywriter, Derek takes a detail-oriented, step-by-step approach to help you shop smarter. Whether it’s nutritional supplements or new scams, he believes an informed consumer is a happy customer.

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