Design Your Next Chapter: A Gentle Transition to Retirement Through Gig Work

Are you familiar with the term ‘gig economy’ and how it’s shaping the way people transition into retirement?

The gig economy refers to short-term contracts, freelancing, or “side-hustles” that differ from the traditional 9-to-5, long-term job. Many companies today prefer to hire freelancers or contract workers instead of full-time permanent employees. And with the rise of digital platforms like Upwork, Fiverr, and TaskRabbit, finding gig work online has never been easier.

You might think gig work is mostly for younger workers, but both millennials and baby boomers are actively participating in this flexible, independent workforce!

Why is this important for those approaching retirement? Because gig work offers the freedom and flexibility to decide how much and when you want to work. For someone nearing retirement who wants to stay engaged, contribute to society, or explore new passions, gig work provides a gentle, adaptable transition.

Some people approach retirement with less saved than they hoped. Gig work not only offers meaningful engagement but can also supplement income during this phase.

What about you? Could retirement be the chance to explore flexible work you’re passionate about? Maybe you’d like to ‘give back’ by supporting non-profits or community initiatives on your own terms.

Examples of gig economy jobs include:

• Delivery or ridesharing

• Rental hosting (think Airbnb)

• Temporary labor or house-sitting

• Skilled freelance roles like writing, graphic or web design, consulting

• Tutoring or teaching online

• Pet sitting or dog walking

• Event planning or assisting

• Virtual assistant or administrative support

• Photography or videography gigs

• Handmade craft sales on platforms like Etsy

This type of work often offers short-term assignments, remote options, and schedule flexibility—ideal for crafting a retirement rhythm that suits you.

It’s also important to recognize some challenges: gig work may lack traditional benefits or income stability, so planning accordingly is wise. Still, the flexibility and autonomy it offers can make the transition rewarding both financially and emotionally.

What kind of retirement transition do you hope for? Would you continue in your current field, or is this a chance to try something new? Either way, your dreams are possible.

Keep an open mind, think creatively, and follow what excites you. You never know how your passions and the world’s needs might weave together in unexpected, fulfilling ways!

Retirement is a new beginning. If you’re considering gig work as part of your next chapter, I’d be glad to help you explore the path forward.

10 Steps to Get on the Path to a Happy Retirement

When it comes to retirement preparation, the first thing that seems to come to mind for people is finances. Of course, the money matters are a critical part of being able to retire and determine when you will retire. After that is established, however, there is so much beyond financial preparation that you can do to ensure a happy retirement. We all know money doesn’t buy happiness, so let’s not stop at financial preparation when it comes to retirement! Your happiness in retirement is worth the effort of truly investing in your future emotional well-being.

How do you get prepared? Here are 10 steps to guide you as you consider, not only what your retirement will look like practically, but how you want to FEEL in your retirement.

1.Define your desires

Are there strengths that you want to develop? What do you want to do with your spare time? Purpose brings meaning to our lives. Knowing what you want to get out of retirement will allow you to construct a post-retirement life that is fulfilling. Make a bucket list and start checking them off while you have the energy, health and money to do so.

2. Define how much you want to work/volunteer

Could it help to have some structure and out-of-home involvement to make your transition into retirement go smoothly? Your retirement is yours to shape. Customize your life to what will serve you best. This could look like part-time work, or voluntary community involvement.

3. Grace for the transition

Moving into retirement is a big life transition and transitions are not always smooth or easy. Knowing this ahead of time can help you prepare mentally for the ups and down. What supports can you set up in advance that will give you the space to work through difficult emotions as they arise? Communicating clearly with your partner or people you are in close relationship with about your expectations for retirement is one of these critical pieces that can be extremely supportive to your transition.

4. Develop a routine

Rhythms allow us to feel safe and secure. Up until now your rhythm may have been externally imposed by having a job. Creating a customized structure for your day and an overall flow for your weekdays are good ways to maintain groundedness in retirement.

5. Exercise your mind

If you were used to problem solving or being actively engaged all day through your work, you may notice that you will need to seek out ways to actively challenge your mind in retirement . This could be by learning a new language or a new instrument, or it could be through mindfulness meditation exercises. There are many ways to exercise your mind - choose the ways that excite you most.

6. Keep physically active

Find ways to move your body every day that feel good for you. Take a walk with a friend a few times a week, or maybe there’s a gentle yoga class you can attend in your community. Staying physically active is imperative for emotional well-being.

7. Eat well

Investing in your overall well-being by being mindful of eating nourishing meals contributes massively to your emotional well-being. We are what we eat. Give your body the fuel that it needs to provide you with a happy healthy body so you continue to be active.

8. Seek out social support

If the majority of your socializing has come from your place of work, you may be feeling lost in retirement - feeling a lack of connection. Seeking out the support you need could look like being honest with your partner or close friends in regards to how you are feeling. It could also look like getting involved in your community in ways that allow you to meet new people, or perhaps rekindling old friendships.

9. Push your limits

Challenging yourself is stimulating. What better time to create new goals for your personal growth! View retirement as the beginning of a journey. Open your mind to the possibilities that exist outside of your current capabilities.

10. Give back to the community

Taking the focus off of ourselves and serving others is so healthy for our mental well-being. The joy of giving is truly unmatched, and your community will benefit from the generosity of your heart.

By integrating these 10 actions as you prepare for retirement, you’ll ensure that you find yourself enjoying the retirement of your dreams. Remember, it’s a process. Change takes time, but if you’re steering in the direction of your deepest desires, the journey is bound to be fulfilling.

For more support as you prepare for your transition into retirement, send me an email at marielle@redworkscoaching.com. As an executive and personal coach who specializes in supporting people through the emotional transition to retirement, it is my pleasure to assist you.

Why we struggle with the transition into a post-carreer life

Your retirement years should give you the best opportunities to rekindle old passions and discover new ones. However, research has shown that almost half of the people entering into retirement struggle with transitioning into a post-career life.

Why is this!?

👉 Retirement is more than just finances
Although many pre-retirees are concerned about their finances, money isn't the only thing on their minds. The impact of the non-financial issues like emotional, psychological and social factors plays a big role in your successful retirement.
👉 Retirement is commonly an emotional time

Whether it’s missing the ‘comfort’ of a schedule, losing your identity or a sense of purpose, it’s common for people adjusting to retirement to experience a range of worries and fears.

What’s the solution? Plan ahead and manage your transition well. If you’re not sure where to start, sign up for my Power Up Your Retirement course! You’ll generate insights, gain clarity and create a game plan to discover your best path to a fulfilling retirement. Register now > https://www.powerupyourretirement.com/

Tip #4 to Get Ready to Rediscover Yourself in Retirement

Do you desire joy and a sense of purpose? Then the best thing you can do is prepare for the emotional and psychological impacts of your post-career life! Preparing for a purpose-filled retirement is not all about the money. 💸

Here is tip #4 to help make your transition a smooth one:

✅ Share your retirement plans with your partner or family
If you have a partner, it’s very important to be on the same page when it comes to plans. Share your ideas with your children or trusted friends. Feeling supported is important.

There are key elements that need to be considered to plan for a smooth transition and a happy retirement.

You don’t have to do this alone. I can help you get there.

Find out how with the Power UP Your Retirement Lifestyle Program.

Special pricing to get you going. Save $300 until January 31.

Tip #3 to Get Ready to Rediscover Yourself in Retirement

Do you desire joy and a sense of purpose? Then the best thing you can do is prepare for the emotional and psychological impacts of your post-career life! Preparing for a purpose-filled retirement is not all about the money. 💸

Here is tip #3 to help make your transition a smooth one:

✅ Create a plan and set goals
If you think preparing financially is the only type of planning and goal setting you need to do, think again! Preparing and planning for the emotional and psychological impacts of retirement and your lifestyle is key.

There are key elements that need to be considered to plan for a smooth transition and a happy retirement.

You don’t have to do this alone.

I can help you get there.

Find out how with the Power UP Your Retirement Lifestyle Program

Special pricing to get you going.

Tip #2 to Get Ready to Rediscover Yourself in Retirement

Do you desire joy and a sense of purpose? Then the best thing you can do is prepare for the emotional and psychological impacts of your post-career life! Preparing for a purpose-filled retirement is not all about the money. 💸

Here is tip #2 to help make your transition a smooth one:

✅ Think about what you want to do in retirement.
Getting stuck in default mode makes for an unhappy retirement. This is your chance to pursue your dreams!

There are key elements that need to be considered to plan for a smooth transition and a happy retirement.

You don’t have to do this alone. I can help you get there.

Find out how with the Power UP Your Retirement Lifestyle Program

Special pricing to get you going.

Tip #1 to Get Ready to Rediscover Yourself in Retirement

Do you desire joy and a sense of purpose? Then the best thing you can do is prepare for the emotional and psychological impacts of your post-career life! Preparing for a purpose-filled retirement is not all about the money. 💸

Here is tip #1 to help make your transition a smooth one:

✅ Start thinking about your retirement 1-5 years in advance.
If you’re going to be making big lifestyle changes like moving or travelling, your key to success is thinking it through well in advance.

There are key elements that need to be considered to plan for a smooth transition and a happy retirement.

You don’t have to do this alone. I can help you get there.

Find out how with the Power UP Your Retirement Lifestyle Program

Special pricing to get you going.

Rediscover Yourself in Retirement

Are you a year or two away from retirement but not sure what your retirement will look like?

People don’t realize that the transition to retirement can be difficult.

There are key elements that need to be considered to plan for a smooth transition and a happy retirement.

You don’t have to do this alone.

I can help you get there.

Find out how with our Power UP Your Retirement Lifestyle Program

Special pricing to get you going.