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  • Writer's pictureJeanne and James Bellew

Part 2: Retirement Reimagined — Finding Purpose and Income Through Freelancing


Welcome back!

In Part 1 of our series, "Retirement Reimagined — How Retirement Has Evolved," we explored retirement and the changes afoot. We've seen a profound shift in retirement paradigms, where traditional notions of leisure have given way to a more dynamic and purpose-driven lifestyle.

This shift is underpinned by a recognition of increased lifespans, the need for financial stability, and a growing desire for purpose.

We revealed statistics that show diverse retirement experiences, from financial challenges to well-being.

Today's retirement strategies, in turn, emphasize financial security, part-time work, healthcare planning, and the pursuit of meaningful endeavors.

As we delve further into our series, "Retirement Reimagined — Part 2," we explore the challenges confronting retirees today and how freelancing can combat these challenges.

Personal Note – I, like James, have chosen freelancing to embark on my next chapter of life. In this article, I will share why I've embraced freelancing and become a coach for new freelancers working on talent marketplace platforms. So, why did I opt for freelancing to transition from full-time work to retirement.. someday? 😉

  • After four "black swan" events (dot com bust, 9/11, the recession, the pandemic), we were ready to move on and experience the world.

  • We're healthy NOW.

  • We wanted to live abroad and travel.

  • While we have savings and investments, we weren't ready to live on a fixed income and be able to live the way we wanted.

  • Working was always meaningful to me — having expertise, being of service, having collegial relationships, and challenging myself to keep getting better for myself and others.

  • I didn't see a way to occupy myself in a meaningful life. My body and mind are strong and capable, with much to give, and too much downtime isn't good for me.

The Reality of Retirement

Retirement isn't always the idyllic image of endless leisure that has been traditionally portrayed. A more complex story includes well-being, satisfaction, loneliness, purpose, and financial support.

Well-being and Satisfaction: Like any significant life transition, retirement affects individuals differently. While some people thrive and flourish in their post-career years, others find the transition more challenging, often leading to dissatisfaction and unhappiness that can sometimes exacerbate bad habits.

For those who thrive in retirement, it's often a time of renewal and self-discovery, embracing newfound freedom and maintaining strong social connections.

On the flip side, some retirees struggle with losing identity and purpose, leading to dissatisfaction and unhappiness, prompting some to turn to unhealthy habits as a coping mechanism. The key to a satisfying retirement often lies in finding purpose, maintaining social connections, and staying mentally and physically active.

Actively seeking new activities and opportunities helps people experience a smoother transition and greater life satisfaction.

Loneliness: Loneliness has become a prevalent issue in retirement, as social circles can shrink and the workplace, a significant source of social interaction, is left behind. Retirement loneliness can arise in unexpected ways:

  • Being unable to shift out of "work mode" and relax, especially if you were a leader or an entrepreneur during your work life.

  • Anxiety about having too much extra time on your hands.

  • Finding it challenging to fill your days with meaningful activities

  • Losing part of your identity

  • Experiencing a decrease in how useful or necessary you were when working can wreak havoc on self-confidence.

  • Anxiety over finances without a usual paycheck to spend, especially if you're living off of Social Security and don't have adequate funds set aside for retirement.

Freelance — Experiencing A Sense of Belonging and Companionship

Freelancing, using the skills and talents you've amassed over many years to continue providing services on your schedule from wherever you want, is a way to fight the loneliness that can come from ending such an essential era.

When you are needed and valued for your contributions and form meaningful relationships through freelancing, you combat the loneliness that can haunt retirement.

Freelancing isn't just about work; it's about connection through conversations and collaborative projects that bridge geographical boundaries. As you near the end of your career and consider the years ahead, the connections available through freelancing give you a sense of belonging and purpose and an opportunity to be part of a global community of people who appreciate your expertise.

Freelancing offers the unique opportunity to engage in vibrant exchanges, share insights, and build lasting connections with clients, colleagues, and collaborators worldwide.

Loss of Purpose — While many people get happier as they age, many in retirement also grapple with a sense of purposelessness as they navigate their newfound freedom without the daily work structure. We've been told that we want to stop working.

However, work gives us a sense of purpose and a way to use skills and talents to help others, to be engaged, and can be a big part of our identity in the world. Losing work can be akin to losing identity.

Considering your future without work before no longer working can have very positive effects. In other words, planning for retirement and preparing for your transition before stopping work is a positive way to enter your new phase of life with meaning and purpose.

Freelance — The Pursuit of Purpose

Pursuing purpose emerges as a powerful antidote to retirees' challenges. It is the linchpin of a satisfying retirement, enhancing mental and emotional well-being.

Freelancing in retirement offers a unique and compelling pathway to pursue purpose. It's a means to remain actively engaged, applying your skills and expertise to projects that align with your skills, personal passions, and values. Whether writing, consulting, designing, or offering specialized services, freelancing empowers you to share your knowledge and experience with the world.

This sense of contribution provides financial support and a profound sense of fulfillment. Freelancers like me find that the projects they choose to work on resonate with their interests, enabling them to make a positive impact while remaining mentally and emotionally engaged.

Freelancing can serve as a conduit for purposeful living, transforming retirement into a phase of continued growth, significance, and newfound meaning.

Financial Insecurity — Financial concerns can cast a shadow over retirement, particularly for those who aren't prepared or are living on fixed incomes.

Financial insecurity during retirement can be a challenging and emotionally taxing experience, particularly for those who haven't saved enough or must rely on a fixed income after a career of financial stability. The shift from a steady paycheck to a more constrained financial situation can lead to feelings of anxiety, stress, and uncertainty. It often forces retirees to make difficult choices, potentially sacrificing their desired quality of life or postponing lifelong dreams.

Coping with these financial constraints can be incredibly frustrating regarding healthcare costs, unexpected expenses, or simply maintaining a standard of living they once enjoyed.

Freelance — Income Diversification.

The transition from a lifetime of financial comfort to a state of insecurity underscores the critical importance of effective retirement planning. The change also emphasizes the need for innovative strategies, like freelancing, to bolster financial stability and enhance the overall retirement experience.

Freelancing in retirement serves as a powerful catalyst for income diversification. Retirees can tap into their skills, knowledge, and expertise to generate income from multiple sources.

Diversification lessens the financial reliance on a single income stream, such as pensions or Social Security, which can be precarious in today's economic landscape, and it can also support not drawing down retirement savings.

By freelancing, you can create a portfolio of projects, clients, and income streams that provide financial stability and flexibility. This additional income not only helps cover daily expenses, M&M money (massages and margaritas), and unexpected costs but also empowers you to explore new opportunities, pursue passions, and enhance your overall quality of life during retirement or as you plan to retire.

A Final Thought

As we bring Part 2 of our series, "Retirement Reimagined — Finding Purpose and Income Through Freelancing," to a close, we've uncovered a vital piece of the retirement puzzle: the quest for purpose and financial support.

So far, we’ve looked at why individuals harness their skills, passions, and experiences to discover purpose and generate income through freelancing.

Now, as we transition to Part 3, "Retirement Reimagined — Freelancing: What Do I Do Now?" we step further into the world of freelancing.

In this final installment, we'll delve deeper into the practical aspects, opportunities, and insights that empower retirees and those planning their next chapter to embrace freelancing.

Freelancing can provide renewed purpose and financial support, transforming your next chapter into a fulfilling and financially supported post-career adventure. So, join us in Part 3 as we navigate the path of freelancing and chart a course for a wonderful, fun, and engaging next act. 😊

Pura Vida! 🌺


1. The Roots of Loneliness Project, Loneliness During Retirement: When The Years Aren’t So Golden, 2023

2. Barefoot Consultants, Income Diversification, It’s not just for Retirement, 10.06. 2023

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Oct 11, 2023
Rated 5 out of 5 stars.

Love your writing! It was SOOOOO nice of taking your time to meet me this week. I am incredibly grateful!

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