🛟 Ask Sarah Anything:What If the ‘Fresh Start’ You Need Is the One You’ve Been Avoiding?

Dear Sarah,

I’m a 56‑year‑old man living in Towson. Recently, my friend told me she is divorcing her husband of the past 20 years and she is beginning to date again. In a way, I'm jealous that she's getting a fresh start to her life. And it’s complicating things for my life. I feel like I don't deserve a fresh start because I never really had a start to begin with. I never got married. I've moved from career to career, but nothing that I felt connected to. Maybe I still don't know who I am or what I really want. I'm not unhappy with my life but I'm not really satisfied. I'm not even sure what question to ask.

How the hell do I start over when I never really started?

Signed,

More than a midlife crisis

Dear More than a midlife crisis

First, thank you for your honesty. You’re speaking a truth many people feel but rarely say out loud. There’s a quiet ache in your words, and a kind of bravery too. It takes guts to admit you're not sure who you are or what you want. And here’s the thing: that’s not the end of the story. It’s the start of a new one.

What you’re asking for is to start a new chapter. Writers don’t need permission to start a new chapter in their books, and you don’t need permission either.

You said something that stuck with me: “I feel like I don’t deserve a fresh start because I never really had a start to begin with.” That belief is what’s keeping you stuck. It’s not that you don’t deserve a fresh start. You’ve been holding your life at arm’s length, waiting for some official “beginning” to make it real. But life isn’t a highway, it doesn’t give us neat entry points. Sometimes the start is simply the moment we stop drifting and decide to show up.

You’re not alone in feeling like you’ve floated through jobs, or missed key milestones. But fulfillment doesn’t come from checking the boxes of marriage or career. It comes from alignment. From getting curious about who you are now, what lights you up now, and what values you want to shape the next chapter.

So how do you start over when you feel like you never really started?

You stop waiting for permission. You stop comparing your life to anyone else’s, unless you’re using it to collect information like “I want that for myself” or “I don’t want that for myself.” Stop focusing on what you’ve “missed” (even the thought that you missed anything is a limiting belief), and start asking what’s possible from here.

You get curious, not critical. You allow the grief and regret to move through but you don’t let them write your future.

Here are three places to begin:

1. Reflect – Not on what you didn’t do, but on the moments that did make you feel alive. What were you doing? Who were you with?

2. Experiment – Try new things without needing them to be the “thing.” Take a class, join a group, go somewhere different. Action clarifies identity.

3. Connect – Talk to a therapist, coach, or group where you can speak freely. You don’t need to do this alone.

You don’t need to know exactly who you are to begin. You just need to be willing to find out. And that, my friend, is one hell of a start.

With heart, Sarah Curnoles
Breakup & Life Coach

P.S. Feeling stuck? Wrestling with your own “where do I even begin?” moment? I’d love to hear from you. Send your questions to me, and I might just answer them in a future column. You’re not alone, and your story matters. Email your question to [email protected]

P.P.S. If you're ready to envision a fresh start (with a cocktail in hand), join me for my Vision Board Workshop with Bespoke Cocktails on July 20. It’s the perfect blend of clarity, creativity, and connection. Come sip something magical and design the second half of your year with intention.