How to Live Successfully as a Retired Workaholic

How to Live Successfully as a Retired Workaholic

Retired workaholic or planning to retire in a few years and are concerned about the transition? You love to work. Work gives you a sense of purpose in life. The idea of working beyond retirement age doesn’t bother you.

The question you ask is, “How do I retire well when working is my life?

Follow the 7 steps below to keep work a priority while still pursuing a life of freedom and flexibility. But first, let’s start with a definition:

What Is a Retired Workaholic?

A “retired” workaholic is someone who continues to stay busy earning money beyond the point of official retirement and insists on never missing a day of work. 

Such a definition might describe your plan, but you’ve probably heard stuff about retirement that worries you — two scenarios in particular.

Does “Retire Gracefully” Mean I’ll Be Doing Little to No Work?

As a retired workaholic, it’s not easy to transition into a life in which you’re detached from work.

If you’re planning to retire in a few years, you might fear a lifestyle that bores you, one in which you feel like you’ll go crazy because you have nothing to do!

If you’re already retired, you might be experiencing this scenario now.

Controlling Your Schedule as a Retired Workaholic

Or you might picture yourself working a lot. You want to continue to earn money, live with a purpose, and stay productive.

The problem is, someone else controls your schedule. You spend much of your waking hours working, and you want to try to stay healthy. Your family might get upset with you because you’re supposed to be retired, right?

As a workaholic, you feel the drive to continue that lifestyle. But you realize that you need to attend to other areas of your life, such as spending time with family and nurturing friendships.

And that’s understandable.

I view myself as a workaholic. So, I can relate. I feel like I need to be busy all the time. I live with a “no days off” mentality. However, I still strive for balance.

You can also live that kind of life, but first, let’s reflect on the idea of being in control of your workday. What might that look like for you?

Maybe it’s this:

Imagine you find a work-from-home job. You can take a break when you want, for however long you please. That restrictive 9 to 5 schedule is a distant memory. You don’t have to struggle to arrive at the office at a certain time.

The new retired you looks even happier, feels more confident and relaxed, and takes control of daily tasks. As a result, you’re sitting at the table with family for each meal every single day!

You realize how precious time is, knowing you’ll never get these moments back.

The following steps outline how you, as a workaholic, can successfully “retire.” What you’re doing is reinventing yourself in retirement by enjoying a new kind of work. You’ll still make a difference and earn income, but you’ll set the hours you work and decide where you’ll perform the tasks.

The Seven-Step Process to Live Successfully as a Retired Workaholic

Step # 1: Set Goals: How Specifically Will You Live as a Retired Workaholic?

National Hockey League superstar Wayne Gretzky once said,

“I skate
to where the puck
is going to be…”

Such a quote inspires us to think ahead. Whether you’re a few years away from retirement or already at that point, set goals—for both work and family life— that are reasonable and measurable.

Maybe you block out some time each evening that you dedicate to spending with loved ones.

If you start an online business, how many hours will you put in each day?

Write out those goals and keep them visible for reinforcement.

Step # 2: Consider Pursuing a Flexible Job(s) in Which You Own Your Schedule

The world of computers and the internet makes working a flexible schedule possible. Examples of such work include:

  • Freelance Writing
  • Online Business
  • Online Research
  • Social Media Marketing
  • Money-making Blog and/or Website

Step # 3: Reflect on Your Experience and Choose Your Niche

Ask yourself…

  • What do I enjoy doing?
  • What background and experience do I have?
  • What areas do I find the most interest in or have a passion for?

The niche or areas you choose could involve any type of work.

Step # 4: Reinforce or Renew Your Understanding of the Internet

easing into retirementAn example here might be learning how to create social media advertisements, such as in Facebook Ads Manager. 

Another skill, which I’m developing, is how to build a website through Solo Build It!. You might want to know how to create and manage your own site or individual blog.

Step # 5: Learn the Necessary Skills

Are you looking to build an online, work-from-home business? You’ll want to draw internet traffic through a keyword strategy known as search engine optimization. Other skills include:

  • Writing sales copy
  •  Online research
  •  Marketing yourself

Step # 6: Practice Your Chosen Craft

How to Live Successfully as a Retired WorkaholicPractice your craft and maintain consistency and discipline by doing some tasks every day in your chosen niche. For me, it’s writing. Practicing also involves writing samples and building my portfolio.

Step # 7: Maintain Accountability While Striving to Maintain Freedom and Flexibility

To stay accountable to your plan, sit down with your family or those closest to you. Or choose an accountability partner whom you can meet with regularly. During those meetings, evaluate your success as a retired workaholic in terms of how you manage your time, and so forth.

Can a Workaholic Retire?

Can workaholics really retire? The answer is—absolutely! But that doesn’t mean you have to stop working. Imagine all this is really possible. You’re still earning money, feeling productive, and doing meaningful work. The difference is, you’re not tied to your schedule.

How can a workaholic retire?

You continue as a dedicated, hard worker in your retirement age, but set your own work hours. This will give you a great opportunity to make money as well as spend more time with family and friends. 

Working through the above steps will help you navigate that journey.

How to Live Successfully as a Retired WorkaholicHow to Live Successfully as a Retired WorkaholicHow to Live Successfully as a Retired WorkaholicHow to Live Successfully as a Retired Workaholic
Joseph Ciccanti

Joseph Ciccanti

Joseph Ciccanti is a freelance writer from Dagsboro Delaware whose articles have been published online and in print. He has written about travel-related topics as well as ones focused on skills and motivation to write. Joseph's passion for writing also involves helping people navigate life's challenges with information on his Solo Build It! website, In addition to building a freelance and online business, Joseph loves to read, travel, and enjoy the outdoors and nature while walking and jogging.
Joseph Ciccanti

Latest posts by Joseph Ciccanti (see all)