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.