Back in second grade, it didn’t really matter much if you failed to make a decision. If one of your parents called out into the back yard to ask if you wanted a PB&J or grilled cheese sandwich for lunch and you were intent on climbing the tree and didn’t answer, you suffered no lasting harm from being served your second choice lunch option that day. But things are different now that you’re a business owner.

After the grueling pace of graduate school, obtaining that advanced degree, and finding a great course for your professional career  – you can finally turn your attention to other life choices. One choice that you’ll be faced with is what to do with the substantial student loan debt. More importantly is, how do you balance enjoying life while starting to pay-off those looming large loans?

Life is complicated these days. And if you’re part of the sandwich generation, with a parent 65 or older and either raising a child under 18 or supporting an adult child, then calling life complicated may feel like a ridiculous understatement. But while being squeezed in the middle will never be easy, there are a few steps you can take to manage your financial and emotional risks.

Are you caught in the middle between supporting children and caring for aging parents? At a time when your career is reaching a peak and you are looking ahead to your own retirement, you may find yourself having to help your children with college expenses or supporting them during a job search while also looking after the needs of your aging parents. Squeezed in the middle, you've joined the ranks of the "sandwich generation."

There are times when imagining the worst-case scenario helps you prepare most effectively for the best case. The transition of a family or closely-held business is one of those times.

Ask yourself, why is it that while Harvard Business School reports at least half of all companies in the US are family businesses - and just over half of all publicly listed companies in the US are family owned - that the most-cited family business statistic is from John Ward’s seminal study finding only 30% of firms survive through the second generation, 13% survive the third generation, and only 3% survive beyond that?

The Family Business Institute identifies a major cause as the failure to imagine and plan for worst-case situations that could dramatically affect not only ownership succession, but management succession planning and leadership development as well.

Your marriage isn’t working - you respect each other but have drifted apart over the years for whatever reason. Now you and your spouse have decided to divorce and close this chapter of your lives. You’ve heard the stories and perhaps witnessed a few horrors through friends or family who have divorced; that doesn’t mean you need to have the same experience.

If you have ever recycled at home, avoided products made overseas by sweatshop labor, grown your own vegetables, supported gender and racial diversity, or owned a fuel-efficient car, then you may be surprised to discover your investments can be working against your values. Do you know what’s in your portfolio? How can you find out what your money is supporting?

Your annual physical checkup and health screenings are scheduled. Your dental checkups, and perhaps those for your spouse and children, are on your calendar or smartphone. Yet many people fail to schedule time for a regular financial health checkup. 

Whether you prefer to block out some time each month or review your financial goals annually, here is what you need to do at least once a year to make sure your money is working hard for you, and that you address the goals most important to you and your family.

Retirement plans demonstrate the wisdom of the proverb “two heads are better than one” — a proverb that always brings to mind the music from the classic Sesame Street video. Now the “two heads” can be you and your spouse, or you and your financial advisor, but you can also benefit from encouraging a dialogue between the income-you and the spending-you.

Financial headlines can be hazardous to your sleep health in retirement. It is easy to get the jitters and start worrying that you should do something, anything but stay on your current financial course. Yet it rarely makes sense to panic and sell your holdings. Over the years I have developed a list of five ways to help you avoid the sleepless nights in retirement that financial headlines can bring.