3 Questions To Ask Before Unretiring So Your Dream Job Doesn’t Become a Nightmare

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Retirement is what dreams are made of. You finally get to kick back, relax, and pursue all those things you never had time for. But sometimes it isn't what you imagined.

Perhaps you need extra cash, have too much time on your hands, or miss the social connections that come with going to work every day. Maybe it's a little of all of the above. That may have gotten you thinking, should I go back to work in some capacity?

If so, you aren't alone. A recent AARP survey found that 7% of adults over 50 re-entered the workforce, with nearly half citing a need to earn money; 14% said they wanted to stay active. And they're not the only older members of the workforce. A recent study from Pew found that nearly 1 in 5, or 19.2% of Americans over the age of 65, are working, either due to financial necessity or personal preference.

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Those who retire and then return to the workforce are largely doing it part-time, freelancing, consulting, and participating in the gig economy, doing everything from car sharing to delivering groceries.

"Almost 20% of boomers report having a side hustle," says Toni Frana, a career expert at FlexJobs. "Retirement is much more of a transition rather than a hard stop. There are plenty of opportunities out there in terms of the type of work you can do in retirement." To find out what, click here for a list of the top ten gig jobs for retirees.

Returning to the workforce may sound appealing to you. But before you join the ranks of retirees with a job, ask yourself these three questions.

1. What do I need this job to do for me?

An older worker shakes hands with a recruiter.

Your motivation for returning to work will dictate the type of job you look for and, quite honestly, your happiness, which is why the first question you should ask yourself is: What do I need this job to do for me, says Frana.

If you're looking to supplement your income, consider getting a steady part-time job. If you're looking to go back to work more for the social connections, a job in an area you love may be a better fit. If you want to give back, a volunteering role with a small stipend could be the optimal choice.

"Is it must-have income or nice-to-have income? That should be the distinguishing factor," says Frana. "If the money is an essential piece, prioritize jobs with predictable pay and hours. If purpose or flexibility is the goal, then prioritize freelance and project-based work."

2. Will my new income actually cost me?

Mature Businesswoman waiting for job interview.

Assuming you aren't going back to work because you need the cash, the second question you have to ask yourself is: Will this job cost me more than I earn, says Caroline Bruckner, senior professional lecturer at American University. "Start with a cost-benefit analysis," she says. "Everything is a trade-off. What is the trade-off?"

If you return to work part-time and earn enough income, will it cause your Social Security benefits to be taxed or push you into a higher income bracket? Will it cause your Medicare premiums to increase or force you to spend money on work attire or transportation?

"Is it going to adversely impact your benefits, and does that matter? Will it adversely impact your taxes, and does it matter?" says Bruckner. "There are very different answers depending on whether you are on a fixed income or not."

3. Am I up for the challenge?

Just because you want to go back to work doesn't mean you will be able to handle it day in and day out.

Life happens, and that part-time dream job could quickly turn into a nightmare if it's too taxing on your time, body, or mind. That's why the third question you should ask yourself is: Am I up for the challenge?

"I've seen retirees make efforts to go back to work part-time and have challenges due to physical limitations," says Bruckner. "And depending on the nature of the work, I've seen older clients not have the confidence to navigate the digital world."

Set boundaries

If you can answer all those questions and are ready to get to work, Vicki Salemi, a career expert at Monster, says it's important to set boundaries before you start searching for your part-time gig.

"Job seekers need to define what are acceptable hours, physical demands and stress levels before they apply and network," says Salemi.

After all, you do want to have a happy and healthy retirement, both from an emotional and financial perspective, and not end up in a role that forces you to work long hours or causes undue stress.

If you ask yourself these three questions and follow this advice, you are one step closer to achieving that.

Editor's note: This article is part of an ongoing series looking at three questions to ask yourself before making a major financial or lifestyle decision. The other stories in the series are: 3 Questions to Ask Before Deciding if a Roth Conversion Is Right for You, 3 Questions That Reveal If You're Actually Ready to Age in Place, 3 Questions That Determine If You're Actually Ready to Retire Early and 3 Questions to Ensure Your Retirement Nest Egg Is Inflation-Proof.

Donna Fuscaldo is the retirement writer at Kiplinger.com. A writer and editor focused on retirement savings, planning, travel and lifestyle, Donna brings over two decades of experience working with publications including AARP, The Wall Street Journal, Forbes, Investopedia and HerMoney.