Squared Away Next Phase

Updated: May 27, 2020

Last August, my family and I went sailing in the Leeward Islands. Having little sailing experience, we took a sailing course in Galveston, Texas. We learned all sorts of knots, basic sailing skills, and a great deal of unusual terminology. One of the terms that I ran across is “squared away.” Now the term “squared away” originated during the days of the tall ships. “Squared away” meant that the sails were optimally trimmed for maximum use of the wind and thus looked like perfect squares. Now, with the era of tall ships mostly over, the term “squared away” has taken on a more modern definition. It now means to put everything in order or in readiness. So, let’s discuss what it means to get your financial life “squared away” before you sail off into your next phase of life (aka retirement).

Step One: Write it down

Think about what you want your next phase of life to look like. Then write it down. Look at it periodically to see if it still feels right for you and your family. After several readings, you will know if it is realistic and right.

Step Two: Educate yourself

Inform yourself about issues new retirees face. Talk with other retirees, read about retirement issues, and seek advice from a trustworthy financial advisor. Don’t get caught off-guard with the unexpected.

Step Three: Make a budget

Determine how much money you may need by tracking your current spending. Humans are creatures of habit and will most likely continue their current lifestyles. Last year, I restarted my budgeting process and was surprised by the differences between the reality of my spending and my perceptions. Start tracking spending and think about what level of spending keeps you content.

Step Four: Make a financial plan

Now that you know what spending level keeps you content, it is time to make a financial plan. The financial plan will provide you with a roadmap on how to accomplish your goals and stay on track.

Step Five: Monitor your progress.

Regularly review your financial plan and investments. Are you staying on track? Are you following your roadmap? Consider implementing an Investment Policy Statement (IPS). The IPS is your operations manual for your investments.

Step Six: Get your estate in order.

There are four essential legal documents that everyone should have in place:

  • Will

  • Updated beneficiary designations

  • Durable power of attorney

  • Medical power of attorney

Getting these in place early will give you peace of mind and help avoid potentially disastrous outcomes for your family.

Step Seven: Minimize your tax burden

Take advantage of the many tools the law allows to reduce your tax burden. You have worked hard to accumulate your nest egg. Don’t unnecessarily lose purchasing power due to excessive taxes.

Step Eight: Insure yourself

Make sure you are properly insured for reasonable risks. This includes risk of early death, property and casualty losses, longevity and health needs. Don’t let a catastrophic, yet insurable event leave you and/or your spouse destitute or put a burden on your family.

These eight steps are by no means an all-inclusive list, but a good starting point to get yourself “squared away” for your next phase of life. I will write more about these eight steps in future blogs. In the meantime, if you have any questions, please email me at

So, don’t get “broadsided” by the unexpected and catch yourself “run aground” or caught “in irons” with indecision. Get your financial life “squared away.”


Recent Posts

See All