Rebuilding a Life (and Income) in Your 50s

For a long time, I believed I had already found my life’s path. When I first started as a writer in 2000, I thought my dreams had come true. When I published my first book in 2008, I believed I was on a new path to freedom.

I created ideas from nothing and watched them become something real, but after a couple of decades and all the changes in technology, my writing career started to dry up, and I began to wonder if it was time to pursue a new career. And, being in the early part of my 50s, it's easy to look at this sudden unrest in my mind as a bit of a midlife crisis.

I am left asking myself, "What do I do now?"

At this stage of life, I’m not chasing only fulfillment anymore. I’m chasing sustainability. I want to be able to pay my bills, enjoy my life, and hopefully retire someday. The thing is... I keep landing in positions where I am still forced to live that gig life. Is it a message from the universe, or am I just looking in the wrong places?

So, here I am, looking at the world again as though I am on the hunt for my first job. What do I want to do with my life?

Step One: Looking Back Without Getting Stuck There

When you're trying to rebuild your career, it's natural to start with what you've done before.

For me, that meant revisiting:

Retail work

Office jobs

Veterinary and animal boarding work

These weren’t just jobs — they were seasons of my life. Each one taught me something about how I work, what I enjoy, and what drains me.

Retail taught me:

I enjoy helping people

I like visual merchandising

I thrive in creative environments

Office work taught me:

I like structure

I enjoy organizing and problem-solving

I appreciate predictable income

Animal boarding and veterinary work taught me:

I love working with animals

I prefer meaningful environments

I enjoy hands-on, purposeful work

Looking back helped me recognize something important:

My past wasn’t random. It was a collection of clues that matter when you're rebuilding.

Step Two: Accepting That Writing Isn’t Gone — Just Changing

Even though my writing career has slowed, it hasn’t disappeared.

I still:

Self-publish books

Create handmade zines (when I'm feeling crafty)

Sell at events

Work toward writing a viral article

Edit and develop ideas

Writing is still part of me. But I’m learning something that many creatives eventually discover:

Your passion doesn’t always have to be your primary income.

- Ivy Rose

That realization is both freeing and difficult. For years, I built my identity around being a writer. Now, I’m learning to see writing as:

A creative outlet

A supplemental income

A long-term investment

A piece of my life, not the whole of it

And strangely, that shift makes writing feel lighter again. It's less forced and less stressful, in a way.

Step Three: Considering the Gig Life in My 50s

There’s another question I’ve been asking myself honestly:

Can I realistically maintain the gig life long-term? This is where the Universe seems to continue pushing me. I love always having multiple streams of income ... it comes in handy when random bills show up. But it always leaves you with that same risk of living paycheck to paycheck, and I am so over that.

Gig work can be exciting, and there are a lot of fun things you can do that make you money. Some of mine have included:

Reselling

Event selling

Freelance writing

Handmade goods

Self-publishing

But it also comes with:

Income unpredictability

Constant hustle

Emotional highs and lows

Burnout potential... but you can get burned out at ANY job, even if you're only working at one place.

In your 20s and 30s, the hustle can feel energizing, but in your early 50s, sustainability starts to matter more. It's that need for stability that has me reconsidering some of the things I did in the past.

Reselling is one of the ones that I seem to come back to constantly, but I am trying to find new ways to work with this passion for thrifting and bargain hunting.

Reselling has always appealed to me because it combines:

Treasure hunting

Creativity

Flexibility

Entrepreneurship

And unlike some creative pursuits, reselling can produce more consistent income if structured well. But rather than filling my house with totes of product, I am trying to find other sellers who want to have an extra team member on the hunt for them... and, well, also scoring some goods I can upcycle for creative projects, so I am doing more than buying and reselling.

Step Four: Trying Instead of Overthinking

One thing I’ve realized during this process is that you can’t think your way into clarity. You have to try your way into it. Instead of just wondering, I’ve been:

Creating things again that I can test the sales waters with

Selling at events and booking gigs as an oracle reader

Applying for jobs in past fields

Considering entirely new directions

Continuing to write and self-publish

Trying to get back into teaching the things I know to others

Some of these attempts will work. Some won’t. But each one teaches me something, which is my real goal right now. I want to find what works best for my life and my monetary needs.

Step Five: Redefining Passion

We’re often told to “follow your passion.” But at midlife, passion looks different.

Sometimes passion is:

Stability

Meaningful work

Flexible hours

A calmer pace

Less financial stress

What I’m Learning Along the Way

Here are a few things this transition has taught me:

1. It’s okay to reinvent yourself more than once

You are not locked into one identity forever.

2. Past jobs aren’t failures — they’re skill libraries

Everything you’ve done can be used again in new ways.

3. Creative work doesn’t have to carry all the pressure

You can still create without needing it to fund your entire life.

4. Stability is not “giving up”

It’s building something that lasts.

5. Trying things is more powerful than planning endlessly

Clarity comes from motion.

Where I Am Right Now

Right now, I’m in the middle of the process.

I’m still writing.

Still creating.

Still exploring.

Still trying to write that elusive viral article.

Still considering reselling.

Still trying to make it with structured work.

And most importantly — still figuring it out. Finding your path isn’t always about one big moment of clarity... Sometimes it's about quietly, steadily rebuilding your life piece by piece.

Perhaps that’s what passion looks like in your 50s:

Not chasing a dream.

But building a life that works for you... even if it doesn't look the same as your peers.