You Are NOT Ready to Retire Until You Can Answer These 7 Questions

The obvious ones include how you will claim Social Security and whether you have enough money to retire, but there are other issues to think about as well — and some have nothing to do with money.

Woman sitting at a desk wondering.
(Image credit: Getty Images)

You know what they say about timing: It’s everything. That’s especially true about retirement.

COVID-19 has thrown many well-laid retirement plans into disarray. Maybe you planned to work a few more years, but now your industry is in upheaval, and you’re ready to call it quits. Or perhaps retirement was around the corner for you, but now you’re worried about an economic downturn so you plan to stay on the job longer.

Clearly, there’s a lot that goes into deciding your optimal retirement date. It requires a careful analysis of your finances, to be sure that your assets are adequate to support you in the retirement you want.

But there are also deeper, non-financial considerations. Has your industry experienced so much dislocation that remaining in the job doesn’t seem like an option anymore? Will you find meaning and purpose in what you do next?

Finances are only one component of retirement planning. There are emotional considerations as you move into the next stage of your life. You want to make sure that you’re emotionally prepared for retirement, because it may be hard to change course. For that reason, our firm employs a life coach to help our clients work through those emotional issues. I encourage everyone thinking about retirement to work with one too.

Because retirement has so many moving parts, I recommend starting the conversation at least five years before your target date so you have time to make adjustments or rethink your assumptions. To help you get a game plan together, ask yourself these seven questions.


This article was written by and presents the views of our contributing adviser, not the Kiplinger editorial staff. You can check adviser records with the SEC or with FINRA.

Andy Schwartz, CFP®
Principal, Bleakley Financial Group

For over 30 years, Andy Schwartz has provided financial planning and wealth management services to clients throughout the country. As an independent adviser, his advice and guidance is always personalized and focused on the client's success. He is the founder and principal of Bleakley Financial Group, a wealth management firm servicing over $5.5 billion in client brokerage and advisory assets.