But, over the past decade or so, circumstances have been changing, in ways both positive and negative, individually and collectively, in our mindsets and life expectancies as well as the economy.  The upshot has been increased flexibility in the way we think about the various stages of the lifecycle, and the varying degrees to which we engage in learning, working, and leisure at all ages.  Because one size really doesn’t fit all — and despite the additional complexity a less traditional lifecycle can impose on your personal financial plan — I think that’s a good thing.  For more on this, check out this article Take A Break From The Binge by The Motley Fool.

But even if you are 100% sure you have a “can’t fail” idea for a business, actually carrying the whole thing out is scary.  As any retiree will tell you, saying goodbye to the vaunted “steady paycheck” is a big step, and probably especially so in this still uncertain economy. 

Does that mean you shouldn’t do it?  Heck, no.  As the events of the past decade have played out, “employment stability” appears to have evolved into a rather quaint notion, evoking feelings of nostalgia even for many with so-called full-time permanent jobs.  So it could well be that the bigger risk lurks in staying at your current job. 

Risks, risks everywhere.  So what do you do?  Start by reading this:

In the article A top 10 list for all the risk-takers among us, Boston.com’s Scott Kirsner offers up some excellent ideas for mitigating the risks of taking the leap from employed to self-employed.  Check it out before you stop by your boss’ office to say “buh-bye”…

“The goal of this one-day retreat/workshop is to help you gain clarity on the career parameters you should consider to make better career choices for the future.

During the retreat, you will work on self-reflection exercises, alone and in teams, to help you better understand your lifelong career interests, your motivated skills, your behavioral style, and the rewards you want to achieve from your work. At the end of the retreat, we will brainstorm as a group to discover career options that will fit your unique needs.” – Randi Bussin

Click here for more information and to register for an upcoming session!

But a prospective self-employed – especially one whose financial situation has been made more precarious by a layoff — is wise to test the waters first.  Why?  As Small Business Administration (SBA) legend has it, only about half of new businesses survive past year 4.  This SBA article lists the reasons, but they pretty much add up to one thing: cash flow, cash flow, cash flow.

So how to make sure cash from your new business flows in the right direction?  In the Wall Street Journal article Becoming the Boss Can Cost Plenty, a few who’ve recently found themselves in over their heads share what they’ve learned about launching a start-up and how they would do things differently if they had it to do over again.

Guest blogger Helaine Iris, a professional Life and Business coach, helps overwhelmed small business owners take control of their time and finances so they can double their revenues with less stress. Featured in numerous publications, including “O” The Oprah Magazine, Helaine’s dynamic personal coaching style helps entrepreneurs accelerate their businesses with tools that empower, build financial success and create personal transformation.

Here, in her article “The Illusion of Freedom and 3 Dirty Words That Cause It”, she explains how new business owners can find the freedom — financial and otherwise — they seek from self-employment by rethinking what freedom really means to them.

Just about every small business owner I know wants a successful business because they value freedom. Most of us have been employed at some point in our lives and know what it’s like to work for someone else – you’re accountable to them, all your efforts conspire in the direction of making them successful and furthering their vision.

Remembering what it’s like to be employed by someone else offers a stark contrast that probably contributed to the decision to start your business or downright pushed you there. Your time and freedom are highly valued assets.

You knew starting a business would take hard work, and you would put a lot of time in – BUT you were highly motivated and abundantly clear that ultimately, you would have freedom and you would experience your life on your own terms.

There’s nothing wrong with that mindset – freedom is a wonderful reason to be self-employed but guess what? The value of freedom you hold so dear is unbeknownst to you creating an illusion that’s getting in your way.

Here’s how it plays out. You resist three dirty words — structure, discipline, and accountability – because you think they’re the opposite of freedom! But, here’s a secret all successful business owners know – structure, discipline and accountability ARE the foundational building blocks freedom is built on. Until you stop resisting and make friends with structure, discipline and accountability, you’ll never get what you want – freedom.

For some reason many people have an almost allergic reaction to the concepts of structure, discipline and accountability. They feel them to be authoritative, not spontaneous, and dare I say, militaristic. Consequently, resisting these qualities ultimately leads to lack and is one of the root causes of time management problems – which leads to – guess what? Your lack of freedom.

What do you do about this? You take a good look at your relationship with these words and change your thinking. You get help if you need it putting a plan in place so you can overcome the illusion. But, most importantly you remember to the core of why you want to be self-employed in the first place – FREEDOM – and decide to do whatever is necessary to get there.

It’s YOUR life… Imagine the possibilities!

Click here to receive a free copy of Helaine’s report “Learn How to Finally Break Through Overwhelm, and Become a Prosperous, Stress-Free Business Owner”.

Photo by Fabienne D.

Already a major challenge for career changers — especially the self-employed and other small business owners — health care just became even more of a wildcard with the recent passage of the new reform bill.  The news is not all bad, just new, and that means it may take a bit of extra effort to understand what it all means.   In her article The Good and Bad in Health Care Reform for Small Businesses, USA Today’s Rhonda Abrams breaks it down for us.

First, readers of the blog have probably heard me say it before: I believe that people need to adopt entirely different money management strategies in order to be successful when they make the leap from full-time employee to self-employed.  (See related posts.) But to my knowledge, the Freelance Finance system explained in The Money Book is the first complete personal finance system for “people with not-so-regular jobs”. So I’m thrilled to have a one-stop-shop resource I can recommend to my self-employed clients.

I’m also pleased to have played a small part in the project coming to fruition, and to be quoted in the book (see page 196!) When Joe contacted me about a year ago during the research phase of the book, I was more than willing to share what I’d learned, both as a self-employed and a financial planner, if — I must confess — a tad mystified by the monkey metaphor. (Read the book! Or check out the March 2010 edition of The New Means News, coming soon.)

Finally, it’s especially gratifying to have been involved in a project that made Liz Pulliam Weston’s list of 5 Money Books That are Worth Every Penny in her recent MSN article. I’ve been following — and continually impressed by — Liz since she spoke on credit reporting at the NH Jump$tart MoneySmarts Teacher conference a few years back. Congratulations to Joseph D’Agnese and Denise Kiernan on having earned such high praise for their work shedding light on this topic, which grows increasingly important as the ranks of independent workers expand.

In 2003, I left my Silicon Valley career behind to open a bookstore in Sacramento.  My goal was to create a passive income business so that I could become a novelist!  

Before I quit my job, I spent a year building my business plan. At the same time, I was tucking away as much money as I could and cutting my expenses. I knew that I wouldn’t earn a Silicon Valley income right away, so it was important to have a year’s worth of living expenses in the bank.

Right around that time, my husband was offered a job transfer up to Sacramento, about 100 miles from where I lived in the Bay Area. I saw that as an opportunity to cut our expenses dramatically since the home prices and cost of living in Sacramento were at least 2/3 less than what we were spending in the bay area. So I sold my house and moved up north—and I’d do it all over again as it was a smart way to prepare for the big transition.

I also opened up a line of credit. I didn’t need it, but wanted to have access to it just in case. One thing the books don’t tell you is that when you quit your job and start a business, you have to reestablish credit. Without verifiable income from a paycheck, it can be much harder to get access to money. I highly recommend getting it before you need it!

So I had my financial and business plan firmly in place.  But the Universe had a different plan for me. Here’s a quick run-down on what’s happened since:

1. Opening a retail store in a lousy location (no street visibility) provided an excellent training ground for small business marketing.

2. I quickly discovered that I am a lousy novelist–not nearly enough imagination.

3. Thanks to internet marketing strategies, I got the bookstore website to the top of Google almost instantaneously. I went on to launch BusinessInfoGuide.com, which has since benefited from SEO practices and a slow and steady evolution.

4. It didn’t take long to realize that I hated just about everything involved in owning a retail store–except the marketing (and the endless supply of books!)

5. I caught the nonfiction bug and decided to write books that I wanted to read. My first title was released in 2005, followed by books in 2006, 2008 and 2009. (I missed one year when I had a baby!)

6. Selling the bookstore was one of the best decisions I ever made. My only regret was not doing it sooner–I was ready to let it go.

7. Launching Authority Publishing was the logical culmination of everything I’ve done so far. It’s created an opportunity for me to leverage my publishing experience (bookstore owner, self-published first book, three traditional book contracts, countless information products…) and blend it with my internet marketing experience. It has also forced me to build a team and treat my business as an asset (so I can take a vacation once in a while!) The results have been spectacular and I know that I am exactly where I am supposed to be.

The other thing I know for sure about my journey over the last six years is that I wouldn’t be doing what I am now if I weren’t willing to take some risks. Taking risks involves letting some things go–which is not always easy.

In this economy, I see a lot of people struggling with this concept, essentially beating a dead horse. But it’s important no matter where the economy is headed. If what you’re doing isn’t working or if it’s bringing you down in any way, perhaps it’s time to consider other options–regardless of how much time or money or emotion you have invested in your dead horse.  Often when you’re willing to let go, all kinds of magical things can happen.

Photo by cote

At that point, I was already several years into my practice, but I still got a lot out of listening to even just the second half of Terri’s tips for solo self-employeds.  Her super-practical advice on business planning, legal matters, marketing, operations, finance, and more cuts right to the chase, with a laser focus on the needs of solo entrepreneurs.  I only wish I’d stumbled on her a lot sooner!

So if you’re just starting out, or if you’ve been at it a while and you could use a little help with the “running the business” part of working solo, check out the wealth of resources Terri has to offer. Her recent Working Solo newsletter is a great example, offering 4 Freebies for Soloists. Enjoy!