The Why To of Choosing Self Employment

Choose something that you love to do and you’ll never have to work a day in your life. This ancient proverb, which has been attributed to Confucius (although this is debated), reverberates into the 22nd century and was the epiphany for my choice to hire myself at age 28. In a 2009 study by the Pew Research Center, it was reported that

“Self-employed adults are significantly more satisfied with their jobs than other workers. They’re also more likely to work because they want to and not because they need a paycheck.


The Pew study shows that nearly four-in-ten self-employed workers (39%) say they are “completely satisfied” with their jobs, compared with 28% of all wage or salaried employees.

Here are some of the reasons why the self employed are happy.

Work Style and Life Style .                                                                        Live While Working. This is an interesting phrase. When I was in my early teens, my father sent me to work on a farm one summer and I discovered that life and work intertwined daily. Life didn’t stop at 7 AM and then restart again at 5 PM. This epiphany of an idea led me, before age 30, to start my own enterprise and, to then fine-tune this business model into one that gave me a great deal of flexibility. I took my core skills in writing and design and joined them with a newfound ability to sell, forming my own small ad agency in the process. For nearly 40 years, I was able to grow my business, support my family and still have time during the work day to spend with the kids, go running or otherwise participate in my personal interests. Life didn’t just happen on weekends.

Crafting Your Career, Sculpting Your Life                                                 In the modern American workplace, especially in white collar jobs, people seem consumed with work. Many large corporations build attractive work campuses to encourage people to spend longer time at work. Exercise centers, team building outings and off-site activities are all designed to increase your sense of belonging to something bigger than yourself: i.e. belonging to the company. In fact, you already do owe your time to something bigger than yourself and that is LIFE!. Your family, your friends, your life interests should all take precedence, or at least equal measure, with your work life.

Focus on Opportunity, not Security                                                       ‘Get a good job with good benefits and you’ll have no worries.’ Well, that just ain’t true anymore. Job security went out the window years ago and employee benefits are being trimmed. Want job security? Hire yourself, create an enterprise that is determined (for the most part) by your own wits, skills and determination. For those truly interested in self employment, the first task is to retrain your brain. Forget job security and start thinking about opportunity. Is there a way you can use your skill set to make money? You won’t really be losing all that much as various studies show that the self employed and employed earn about the same annual median income.Where it really varies is in the long term, where the self employed tend to out-earn their employed peers. The difference is in the freedom to capitalize and build on opportunity.

Determine What You Want From Your Work                                 Over my many years of speaking in front of businesspeople, and working with smaller businesses and professionals, I have seen how making the decision to be self-employed, for the wrong reason, can come back to haunt you.  There are many ways to be self-employed, successful, and happy.

Find a work-style that works for you, for example:

• You like structure and organization at work, but you don’t want it to be someone else’s idea of structure. Then choosing to start a traditional business, perhaps with employees, may suit your life style.

• You like to have direct contact with customers/clients, and enjoy doing the work or creating the product with as little outside interference as possible. Then, perhaps you should consider being an independent contractor or running a solo enterprise.

• You’re interested in wealth accumulation and retiring early enough to enjoy it. Then you’ll probably want to focus on an enterprise that offers passive income potential, such as selling products which offer an ongoing return.

For many self-employed people, success is not only measured by money brought in, but by freedom of ideas, of creativity, and of time to live life.


Tips For Cultivating A Successful Work At Home Career

Successfully working from home is a skill that requires planning, discipline and practice. For the 1099er, especially someone who has always worked at an office, manufactory, retail store or other brick and mortar location, this new work style may be daunting a first.

In this blog, I’m going to share some tips and advice from someone who has worked this way for more than three decades.

But first, let me tell you a little story.

My Early Day’s in the Netherworld

Way back when, on a September morning some 30+ years ago, I found myself unemployed for the first time since age 13. 

I had launched my little ad agency just two months earlier. The first few weeks in this new enterprise were a strange, netherworld time.  I felt a bit lost and directionless, while simultaneously rushing about trying to set up the new business.  There were business cards and stationery to do, a brochure to create and print (remember this was back before the impact of the digital age–– no internet, websites, social media). There were also all the administrative tasks of setting up a basic enterprise: tax ID, business banking account, mercantile licenses, etc.

It was also the summer and my new life had not yet impacted me. The coming of summer in the colder climes of the northeast always brought with it a sense of relaxation, so the impact of going solo had not yet hit me. I was getting free lance work from my former career as a magazine features writer, and had landed a plumb assignment in June that paid most of my bills for the summer. I kept working at the business, writing free lance and even took a long motorcyle adventure with a friend that August, riding from Pennsylvania to the northern tip of Maine.

Then summer ended, my well-paying free lance article was finished and published and I had completed most of the administrative and operational side of the business. I realized there was a rather large void in my work life. As I had done since college days, I began each day at 6AM and went to my desk. Only this time, there were no articles to write, no deadlines from my superiors, no interviews or appointments.

It was a little bit frightening. 

To fend off the panic, I did something that had always worked to calm my uncertainties: make plans. I methodically worked through a marketing plan, a business and home budget and, most importantly, a structured way to go about selling my services. So, I began making a daily schedule.  If there was no external force (bosses, deadlines, etc.) then I had to impose my own structure.  Days were parsed into segments:

• Early morning was dedicated to developing creative materials, improving my portfolio

• Mid-morning was dedicated to going through business directories and creating a call list

• Mid-day was my exercise and fresh air time

• Afternoons were spent in presentations to prospective clients, making cold calls to get presentation appointments, delivering project materials to various vendors (remember, no web, no ftp) and, doing free lance article interviews

• Evenings were spent doing research or writing the occasional free lance article, or when the  opportunity presented itself, making free presentations.

At first, this self-imposed schedule felt a little like wearing someone else’s coat. It seemed to be something that I just put on for protection, After several weeks, however, this schedule created the structure and discipline I needed to keep me motivated, focused and soon, successfully bringing business in the door.

By the end of November, I had two small clients and some sub-contracting copywriting/design work for another one-person ad agency. The latter was excellent experience for me as my only prior advertising position had been as an intern with a major Philadelphia agency. Here, I got to see a small business person operating within my chosen area. I learned what to do and, more importantly, what NOT to do as a solo enterpriser.

Working From Home: Tips for You

The freedom of working from home can also be a curse. If you will not, or cannot, cultivate a disciplined or structured working style, then this may impact your ultimate success. Here are

three essential areas to address.


Planning, in this 1099er’s opinion, is the key to ultimate success for a work from home business. Here are some examples:

  • Develop a solid marketing plan for your enterprise.
  • Plan your day. Get up at the same hour, have a start time for work. Schedule in some outdoor time–– whether that time is used for exercise, outdoor chores, running errands or just fresh air–– breaking at mid-day helps maintain maximum output.
  • Set daily goals and do your best to meet them.


A plan is all well and good, but one needs the WILL to implement it. If you’re the kind of person who is a disciplined self-starter than this should be fairly easy. If you’re not, here are few tricks to help you acquire the needed work discipline.

  • Learn to master distractions. Cultivate the will to pull yourself back into the task when you find your mind drifting.
  • Set deadlines. Create an imaginary boss that wants a particular task done in a set period of time, then go and do it.
  • Organize distractions. Even if you manage to avoid family or household distractions, there are going to be emails, texts and phone calls. Put these into a time slot each day. So that you’re maximizing output of your income-producing tasks.


“You have a routine, until you don’t”, said a celebrity forced out of a job after many years.

Implementing your daily planning faithfully and building your discipline will result in the development of a work at home routine. No matter how technology continues to change the way we work, a solid work routine can serve you for a lifetime–– as it has done for me.