The 3 Keys to Retiring Early and Being Happy

Early retirement is something that many people aspire to their entire lives. But there’s more to retiring early than just turning in your office keys and gathering up all your family pictures from your desk. You also have to think about what early retirement will actually be like and anticipate potential problems — before it’s too late to do anything about them.

Many people who’ve retired early have discovered three areas in which they weren’t adequately prepared. We’ll share them below, along with some ideas for how to address them.

1. Show yourself the money

Quitting your job means giving up your primary source of income, and so it’s important to understand exactly where you’re going to get the money to handle living expenses. Social Security isn’t typically available until your early 60s, so if you’re planning to retire well before that, you’re going to have to identify other sources of cash.

Even those who are fortunate enough to have other financial resources available still have to keep some things in mind. For instance, those who save in tax-favored retirement accounts like IRAs and 401(k)s have to deal with the early withdrawal penalties that often apply to those under age 59 1/2 who take money out. There are exceptions to those rules, but you’ll need to explore them completely in order to determine if they’ll provide enough cash for your expenses. Similarly, if your company offers a pension for retirement purposes, you’ll want to know when it might let you start collecting benefits and whether there are any adverse consequences from taking that money earlier than normal retirement age. The best financial resource is a completely accessible regular investment account, and so planning to have some of your money available is a smart move.

2. Taking care of your health

An even bigger obstacle to early retirement is figuring out how to get healthcare coverage. Most Americans get their healthcare through their jobs, and the ability to keep workplace coverage extends only for a short period after you quit. Meanwhile, Medicare coverage won’t kick in for most people until age 65. That creates a long potential gap during which any serious medical conditions could wipe out your entire savings.

Some solutions include using a spouse’s workplace coverage or seeking to find individual coverage on your own. However, individual coverage is often expensive for those who retire early. Although staying on with a former employer’s coverage under COBRA can work for some people, the relatively short time periods during which employers offer COBRA coverage don’t make it the ideal long-term solution.

3. Keeping your friends and social life

The workplace dominates American culture, and for many, spending time with workmates is a natural extension of their days. That can make retirement scary, as you risk losing the social network that you’ve relied on for decades. Even if you promise to stay in touch, it doesn’t always happen and is sometimes awkward when it does.

Most early retirees who’ve successfully made the transition point to the importance of keeping some of your old friends but making new ones as well. Being retired gives you flexibility that your working friends don’t have, so using your newfound time to meet new people can end up enhancing your social life. Yet it’s smart to keep longtime friends in your corner in order to handle problems that can benefit from someone who knows you well.

Be ready to retire early

Knowing that these early retirement issues are out there is half the battle. By thinking about them beforehand and taking steps to address them, you’ll be in a better position when you walk out of your workplace for the last time.