When it comes to retirement, like many things in life, timing is everything.

Across America, many Boomers are wrestling with the question of when to leave the working world behind. Retire too early and you risk outliving your nest egg; wait too long and you may never get to enjoy retirement at all. It’s a complicated decision, to say the least, and one that is causing many would-be retirees to choose inaction – they simply continue to work without tackling the difficult decision of when to stop. Below are four common reasons workers put off making the decision of when to retire.

Fear of Not Having Enough

The sad truth is, many workers aren’t retiring because they are paralyzed by the fear of not having enough money for their monthly expenses. Unfortunately, many of them may be right. Recent data shows that 64 percent of Americans aren’t saving enough for retirement. Many Baby Boomers have spent years planning to rely on whatever they’ll get from Social Security, only to wake up as they near retirement age and realize they should have been supplementing their monthly retirement income with cash savings and smart investments, too.

According to Nationwide Retirement Institute, nearly half of retirees wish they had been better prepared for the taxes they would pay in their retirement years. In fact, a full 25 percent reported paying thousands more than expected. These surprise expenses can be frustrating at best and downright painful at worst, and they’re getting more and more common as retirees rely on tax-deferred options like 401(k) accounts.

If you’ve ever had a retirement conversation with your spouse that left you both frustrated or confused, it may not surprise you to learn that the majority of married couples find themselves misaligned when it comes to financial values and money management. In fact, 43% of couples are not even on the same page about when to retire.

At first glance, it may seem strange that two people living together – possibly for decades – are saving toward divergent timelines. However, money topics, in general, are common sources of frustration in relationships and are often cited as the main factor in divorce. Today, boomers are divorcing at higher numbers than their parents – often called gray divorce - meaning that the money saved for retirement will have to do double duty in order to serve both spouses when they part ways.

Family Gatherings are Prime Opportunities for Discussions About the Future

Do you subscribe to the belief that family gatherings aren’t an appropriate place to discuss things like politics, religion or money? Many people feel this way, causing them to put off financial discussions about the future for another time. However, when your family is gathered together celebrating Thanksgiving and you’re feeling gratitude for the loved ones around you, it can open the door for important money conversations that impact your family’s future.

Why You Should Never Neglect Estate Planning

Topics such as where your assets will go when you die can be uncomfortable to broach, but estate planning is integral to your family’s financial future. Establishing a thoughtful succession plan using a document like a will or a living trust can benefit your whole family and ensure your wishes will be met. Ideally, you should have these plans in place before an emergency occurs, and while the oldest members of the family are still in good health, both physically and mentally.

There’s More to it Than You May Think

Imagine this: you plant a beautiful flower garden and tend it faithfully for forty years. You protect it from stormy weather and pests, you never pick its beautiful blooms and you don’t traipse through it for fun. You never even get close enough to smell the fragrant flowers or run your hands through them because you’re focused solely on growing them taller and stronger without hindering their progress.