At 56, I’m Starting Over — But I’m Not Starting From Zero

At 56 years old, I’m starting over.

That probably sounds strange coming from someone who has spent 35 years in the music industry.

I’ve worked in radio, including Z100 New York. I’ve worked at Tommy Boy Records. I’ve spent decades as DJ Riddler, performing, producing music, working with artists, promoting events, and building a career in an industry that I’ve loved for most of my life.

So why would I say I’m starting over?

Because the music industry I started in doesn’t exist anymore.

And I’ve realized that if I want to keep moving forward, I can’t spend my time trying to recreate what worked 20 or 30 years ago.

I have to become a student again.

Everything Changed

When I started my career, radio was one of the most powerful ways people discovered new music.

Record labels were the gatekeepers.

DJs broke records.

Physical music mattered.

There was no Spotify. No TikTok. No Instagram. No YouTube.

There definitely wasn’t an algorithm deciding whether thousands of people might see something you created that morning.

Today, an artist can make a record in a bedroom, distribute it around the world, create a video on a phone and potentially reach millions of people without ever stepping inside a radio station or major record label.

Social media changed how we communicate.

Streaming changed how we consume music.

Technology changed how we make it.

And now artificial intelligence is beginning to change the industry all over again.

I could complain about those changes.

I could talk about how things used to be.

Or I can learn.

I choose to learn.

Becoming a Student Again

One of the most humbling parts of reinventing yourself later in life is accepting that experience doesn't mean you know everything.

Sometimes I’m asking people half my age how something works.

And you know what?

That’s okay.

I've been learning more about content creation, social media, digital marketing, streaming platforms, analytics, new technology and the ways artists build audiences today.

I'm also releasing music again and approaching it differently than I would have years ago.

Some things feel completely foreign.

Other things remind me that while the tools have changed, many of the fundamentals haven't.

A great song still matters.

A great story still matters.

Relationships still matter.

Hard work still matters.

Connecting with people still matters.

The delivery system has changed.

The fundamentals haven't.

The Three Things I'm Learning About Starting Over

I've thought a lot about what I'm doing differently during this chapter of my life.

I keep coming back to three things.

1. Tell Your Story

For a long time, I never thought much about telling my own story.

I was too busy living it.

But after 35 years, I've accumulated experiences that belong uniquely to me.

The radio years.

The record-label years.

The clubs.

The records.

The artists.

The successes.

The failures.

The changes I've watched happen in music and nightlife.

Those stories have value precisely because they're mine.

That's something I'm learning about content as well.

You don't have to copy someone else's story.

Tell the one only you can tell.

2. Learn From Other People

Starting over doesn't mean pretending you already have all the answers.

I've been studying what other creators, artists and entrepreneurs are doing.

What works?

Why does it work?

What can I learn from it?

That doesn't mean copying someone else. It means understanding what works today and figuring out how those lessons apply to who you are.

Experience is valuable.

But experience combined with curiosity is even more powerful.

3. Ask for Help

This one isn't always easy.

When you've been doing something for decades, there's an expectation that you're supposed to know what you're doing.

But nobody knows everything.

If someone understands something better than I do, I want to learn from them.

Sometimes that means asking a younger person about a platform I've never used.

Sometimes it means talking to another artist.

Sometimes it's asking someone to look at something I've created and tell me what they really think.

There is no prize for figuring everything out by yourself.

The Most Important Lesson: Just Start

This may be the biggest lesson of all.

People ask:

Where do I start?

My answer is becoming very simple.

You just start.

Don't wait until you're completely ready.

Don't wait until everything is perfect.

Don't wait until you've figured out the entire plan.

Because you probably never will.

Start before you're ready.

Learn.

Make mistakes.

Adjust.

Then keep going.

That's what I'm doing.

Why I'm Sharing This Journey

Over the past few months, I've made a conscious decision to start documenting more of my journey.

Not just the highlights.

I want to talk about what I've learned from 35 years in the music business, but I also want to share what I'm learning right now.

Music.

DJing.

Producing.

The music business.

Nightlife.

Technology.

Content creation.

And what it's like trying to reinvent yourself at 56.

I don't know exactly where all of this will lead.

And strangely enough, that's part of what makes me excited about it.

I'm not trying to recreate the career I had.

I'm trying to discover what the next version of it looks like.

I'm Starting Again, Not Starting From Zero

If you're 40, 50, 60 or older and you've been thinking about changing careers, starting a business, creating something, learning something new or finally pursuing something you've put off, I hope you'll remember this:

Starting over doesn't mean you're back at the beginning.

You're bringing your experience.

Your successes.

Your failures.

Your relationships.

Your mistakes.

Your knowledge.

Your perspective.

Everything you've learned comes with you.

That's the difference between starting over and starting from zero.

At 56, I'm not starting from zero.

I'm starting again—with 35 years of experience coming with me.

And I'm documenting the journey as I go.

Let's see where it takes me.

— DJ Riddler