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4 Ways to Fund Your Second-Act Dreams

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When I speak to people about their second-acts, I often get asked this question, “I’d love to make a switch to my dream semi-retirement job, but I can’t afford it. What should I do?”

I understand their concern. After all, it’s easy to say, “Follow your passion” or “Now is the time to realize your dreams.” But when you have bills to pay and little in savings, your financial reality and second-act plans may not line-up. Training is expensive, new businesses require start-up capital and salaries for people pivoting to something new are far less than those of experienced workers.

Luckily, there are steps you can take to shore up your finances, no matter how challenging your current reality. Here are four to consider:

1. Maximize your employee benefits. While you’re still at your current job, make sure to take full advantage of your employer benefits, because doing so can save you thousands. Even if you already participate in health insurance coverage, you might not be using some of the less popular benefits, such as employee discounts, flexible spending accounts or the company match on your charitable donations.

If you’re hoping to retrain for a second-act career, be sure to take advantage of any opportunities for personal or professional growth. Inquire about tuition reimbursement benefits. And if your employer doesn’t offer tuition reimbursement, they might sponsor other training-related opportunities, such as webinars or reimbursement for industry-related conferences and events. These training experiences can help you master new skills and improve your marketability.

2. Take advantage of free and low-cost training options. Whether you’re thinking about starting a business or looking to hone your skills for a job shift, chances are you’re going to have to invest in some level of training. Fortunately, the options for adult learning have never been more plentiful or affordable. From cooking to coding, there are thousands of online classes you can take at incredibly affordable prices (and sometimes for free) using MOOC’s, massive open online courses, offered by some of the world’s top universities and organizations. And if you prefer to learn in a traditional classroom, there are plenty of affordable options at community colleges and adult continuing education programs.

3. Spend less and save more. Yes, you’ve heard this one before, and yes, it’s easier said than done. But we all have room to cut somewhere. For example, going from a two-car family to a one-car family can result in considerable savings, and might be feasible now that the kids have flown the coop. And speaking of being an empty-nester, do you still really need to subsidize a kid’s cell phone bill or car insurance payments? Making the time to review your savings and budgets can sometimes reveal hundreds or thousands of dollars in needless expenses.

Use technology to help streamline the process. Apps like make it easier to track your finances. helps you find great money-saving deals. And a site like has advice on simplifying your life, so you’ll have more time to enjoy the things that matter.

4. Leverage your housing. For most people, a home is their single biggest expense. If you’re looking to reduce your housing costs, here are a few ways you might be able to slash expenses:

  • Downsize. Moving to a more modest home means less space to manage, fewer upkeep costs and perhaps lower property taxes. The money you save can go straight into savings or be invested into your second-act shift.
  • Rent out a room. If you prefer to stay put in your house, you might want to take on a boarder. (Just be sure to check out the rental laws in your area first.) You can source renters through word of mouth or use a sharing service like, a site that helps match renters over age 40 with suitable rentals. Another alternative is to offer a short-term rental through a company like Airbnb.
  • Board animals. If you’re an animal lover who lives on a large property, you might be able to offer boarding services for dogs or even horses. Here again, be sure to check zoning laws before accepting clients.
  • Work as a property caretaker. Sell your home and live rent-free in exchange for providing property caretaking services. This can be a great way to reduce retirement costs and eliminate almost all your out-of-pocket housing costs. For example, we recently stayed at a chateau in France that is being looked after by a semi-retired couple from Las Vegas. In exchange for taking care of the property and hosting occasional guests, the couple gets to live at the chateau year-round rent-free.

Making adjustments to your budget and lifestyle is rarely a painless process. But by doing so, you’ll be far better prepared to enjoy a second-act career that allows you to work when, where and how you want.

This is a reprint of an article I originally wrote for To read more of my articles on the site, click here.

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