Posted on 02/03/2017

My Journey to Self-Employment: Is Self-Employment Right for Me?

Getting into the nuts and bolts of self-employment. The Work for Yourself@50+ Toolkit will help you decide if working for yourself is right for you and how to go about it, step by step. Call 1-888-339-5617 to request a copy.

OK, let’s take a look at this “Work for Yourself@50+” Toolkit. . . . It’s going to be a quiet weekend. I may as well at least crack the spine on it.

This first section, “Explore Your Options,” looks interesting. It will help me consider if self-employment is really the way I want to go. Well, let’s be honest, with the job market the way it’s looking, unless something really unexpected happens, self-employment looks like the only way to go. So, let me grab a cup of tea. . . .

This toolkit is broken down into five discrete pieces, digestible sections, like the wedges of a pie, beginning with the “Explore Your Options” section I’m going to work on today. Sometimes I feel my options are limited, so I’ll be interested to see what the possibilities really are.

When you’re self-employed, your income comes directly from customers or clients who consume your products or services, instead of an entity for which you are an employee.

Are You Ready To Be Your Own Boss?

The common theme across the spectrum is that you are your own boss. The world is full of us these days; we are temps, sole proprietors, consultants, on-call workers, freelancers, 1099 workers and more. We have the flexibility, freedom and creativity to indulge our dreams and make things happen in the world in a way that we truly care about.

There are a number of ways to approach this world of self-employment. Seems I could create a part-time business, or side gig, in addition to my full-time job; that is, of course, if I had a full-time job. Not bitter, mind you; just transparent. So let’s move on to option two, freelancing or working as a contractor; working on specific projects on behalf of other organizations—that’s me! Then there’s running my own microbusiness, with five or fewer employees offering my products or services. I could create a social enterprise or non-profit organization, with the goal of doing good for the community while also generating a profit.

Now, do I have the stomach for any of this?

I have nothing to invest, therefore nothing to lose by giving it a try. And speaking of nothing to invest, how much do I have to earn in this enterprise to stay afloat?

The Business of Me

I have been walking the tightrope for so long that taking the risk on a new venture no longer raises my blood pressure. After my stint as a professional jobseeker, it seems the regular 9-to-5 with “bennies”, 401(k) and the like is a thing of the past. So I better get on with creating The Business of ME.

Now, mind you, this is a walk on the wild side, not for the faint of heart, so carefully examine your goals and the advantages and challenges of going it alone using the handy worksheets in the Work for Yourself@50+ Toolkit.

But, if you get even just a little thrill from the thought, then maybe this is the path for you. C’mon! Let’s go for it!

Call 1-888-339-5617 to request a copy of the Work for Yourself@50+: 5 Simple Steps to Get You Started toolkit or complete this short form to download your copy now.

Self‑employment may not be the right fit for everyone. But knowing what questions to ask yourself can help guide you to the decision that makes sense for you.

See related blog posts: My Journey to Self-Employment

Michele Higgs

Michele Higgs

Blogger Profile: Michele Higgs is on a journey to self-employment with the help of AARP Foundation’s “Work for Yourself@50+” program. In this blog series, Michele will describe her experience with the program and will walk through the Five Steps to Self-Employment which provides guidance and advice on self-employment. This is the third of a series of blogs she is writing about her experiences with the program.

*Updated 06/26/2017

2 Responses to “My Journey to Self-Employment: Is Self-Employment Right for Me?”

March 05, 2017 at 10:37 pm, Jo said:

Hi, Michele,

I love this new blog. It’s a great idea!

I’m really hurting financially after being laid off from a very well-paying job in 2010. My 40-year career as an editor with a concentration in copy editing ended at that point: Jobs for someone of my age with my skills no longer existed. I was unemployed for four years!

Now I’m collecting social security and have found a part-time job (which I love), but the combined income from those two sources isn’t enough for me. I can’t save a dime; I spend half of my total gross income on rent; I never buy anything except the essentials–groceries, medications, gas, household products, phone and cable charges, insurance, etc. After losing a successful career and an upper-middle-class income, I’m depressed and scared. How will I survive if I live a long life? The money in my IRA won’t be nearly enough.

Here’s what I’d like you to comment on: If I supplement my income by freelancing, my taxes will go up so much–and my tax returns become so much more complicated–that I feel I may as well not bother. What are your thoughts?

Thank you!


April 07, 2017 at 4:37 am, Miichele said:

Hi, Jo,

No excuse for taking so long to respond, but I thank you for writing and I will try to allay your fears, even if I cannot solve the problem. You are in a challenging position, like so many of us, where every day is a calculated dance with disaster.

However, I say if you have found your way into an opportunity that you love, why give it up because you’re afraid of the IRS? Yes, additional taxes will have to be paid; but, it can be worked out.

Think about the ways to offset some of that cost, though. Do you volunteer, can you teach, serve the disabled? What about your volunteer work, how much time do you donate? And goods? We can all clean out and de-clutter our homes; those donations to charity count. For a home-based business, are you sure you’re considering every possible deduction?

Yeah, we’re grown-ups, but I got scared and tapped my Social Security, too. Taxes are beyond my ken; but, try your local Chamber of Commerce, community organizations, or talk with your friends,to get recommendations for someone trustworthy, up-to-date and as passionate about doing taxes as you are about creating a life that works.

Life is too long to live small, Jo. I don’t want to misguide you, but treat yourself sometime. Then you won’t feel as cheated, sad and afraid. Plus, the utility company won’t miss the $10 you shave off your payment every now and then to go to a movie or buy the makings for your favorite dessert. Then invite a fellow traveler over for tea, you may be surprised by what sharing with others does for your spirit..And, do the thing you love; you might create a self-employment opportunity that could turn into something more,The Business of You..Thank you for visiting and for your query. Have at it!

Best to You.


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