Quitting a secure job at a big corporation to go out on your own is one of the most harrowing decisions you can make. I should know -- I just did it and now it feels like I'm working without a safety net for the first time since college. But the change has been good. I'm spending more time with my family, doing something I love, and escaping the constant distraction of corporate pressure and office politics. And the 15-second commute to my home office is nice.

But the change has not been without difficulties. For one, I lost my office and had to start from scratch at home. This meant buying a new laptop, securing a high-speed Internet line, and setting up a fax line. Did you know that home office expenditures such as these are tax-deductible? According to the IRS, you can generally deduct "the business portion of real estate taxes, mortgage interest, rent, utilities, insurance, depreciation, painting, and repairs" from your income taxes. In addition, business expenses like that laptop or fax line are deductible as well if you itemize your tax return. So that's a few hundred dollars a year saved right there.

Obstacles ahead
There are plenty of other challenges. The first major issue I encountered was the loss of health insurance. My company provided me with a Health Savings Account (HSA) and a high-deductible insurance plan from UnitedHealth that I had to replace that with something affordable and reliable. Fortunately, there are a plethora of choices available from respectable providers, and I'm currently poring over the various options. But it looks like another HSA is the way to go.

Why? Well, consider what the sizable premiums for high-coverage, low-deductible health plans are doing when your family is healthy. That's right -- nothing. In 2004, I spent $300 per month on those premiums and less than $1,000 on actual doctor's visits, prescriptions, and the like. The total cost for the year came to nearly $4,500, and it was a year of no major health-care needs.

Last year, my family transferred to a lower-premium plan with much higher deductibles. Including $2,500 of direct costs related to the birth of our second child, we still came out more than $1,000 better off than the year before.

Lower deductibles and out-of-pocket expenses may feel nice at the checkout counter, but those premiums could have been working for you instead of padding the insurance company's pockets. With an HSA, you put money into the account, hosted by nearly any bank you choose, and use it later for health-care costs. Contributions are tax-deductible, the interest earned is tax-free, as are qualified withdrawals to cover health expenses. In the meantime, some banks pay you interest on the funds stashed away, while others let you invest in bonds, mutual funds, or even individual stocks. How Foolish! Tax savings and investment opportunity!

The road ahead
I will soon have the health insurance issue settled, but then it's on to the next life-changing bump on the road to freedom and independence. Once my final paycheck from my old job is processed, I will have to roll over my 401(k) account into my IRA, for example. But that's something I can look forward to, as I've done it before and it represents another opportunity to invest in my future.

That means expanding the core of income-generating stocks that I am pretty sure will still be here when I retire in 30 years, including Bank of America (NYSE:BAC), Coca-Cola (NYSE:KO), and Pfizer (NYSE:PFE). But I will also look for some exciting growth opportunities with perhaps a shorter time horizon to round out my portfolio.

Today, that role is played by stocks like Elan (NYSE:ELN) with its proven multiple sclerosis and prospective Alzheimer's treatments, Intuitive Surgical (NASDAQ:ISRG) and its groundbreaking robotic surgery, and DVD-by-mail rental service Netflix (NASDAQ:NFLX).

High-risk, high-return mutual fund BridgewayAggressive Investors2 (BRAIX) will also see some new cash even though it's my largest single holding. I have full confidence in fund manager John Montgomery and his team, and the fund is currently looking rather cheap, historically speaking.

The Foolish bottom line
Life is full of important choices that can have major effects on your finances. That's why we recently launched our Motley Fool GreenLight service. From money-saving tips to information on how to get started investing to advice on balancing your portfolio, it's a one-stop shop to get your finances in order. I know I'll be turning to the service for my own edification and enrichment. Want to join me? Click here to try GreenLight free for 30 days.

Fool contributor Anders Bylund owns shares in every single company mentioned except for UnitedHealth. You can check out his holdings for yourself if you like. UnitedHealth is a Stock Advisor and Inside Value pick. Netflix is a Stock Advisor pick. Pfizer and Coke are Inside Value picks. Bank of America is an Income Investor pick. Intuitive Surgical is a Rule Breakers pick. Foolishdisclosurewill always keep you covered.