Single Mom at a Crossroads: How to Overcome Self-Doubt and Thrive

Life doesn’t always go as planned, and sometimes, it can feel like you’ve hit a dead end—especially when you’re raising kids on your own. At 36, juggling motherhood without a partner or strong support system can feel overwhelming, leaving you questioning your success and purpose. But is it really failure, or just a new chapter waiting to unfold? How can I rebuild my life, find fulfillment, and prove to myself that it’s not too late to start over?


[adjusts wisdom glasses and leans in with a knowing smile]

DISCLAIMER: Reading this post may cause sudden outbreaks of self-belief, random acts of life-changing decisions, and the dangerous realization that your story is far from over. Side effects may include standing taller, laughing at your former definition of “failure,” and the irresistible urge to prove yourself right instead of proving others wrong.

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Let’s address the elephant in the room: your question assumes “failure” is a permanent state rather than a temporary chapter. I’ve got news for you that might be hard to swallow at first, but will taste like freedom later.

You know what’s wild about calling yourself a “failure” at 36? It’s like declaring the game over when you’re barely past halftime. My completely made-up but eerily accurate research shows that 87% of life’s greatest comeback stories started with someone exactly where you are now—convinced they’ve fumbled the ball beyond recovery, only to discover they were just warming up for their finest play.

The F.A.I.L. Method: Finding Awesome In Life

[taps imaginary chalkboard with experienced teacher energy]

When I work with folks who think they’ve “failed,” I introduce them to my framework—let’s call it the F.A.I.L. Method, which ironically stands for Finding Awesome In Life:

F – Face Reality (Without the Drama)

First, let’s get crystal clear on your situation without the emotional catastrophizing. You’re 36—that’s young in the grand scheme. You have two children—that’s not a burden, that’s a legacy. You have no husband—that’s a statement of current circumstances, not a measure of worth. No one to care for you? That’s a temporary situation, not a life sentence.

Take my fictional but truth-based client Sarah. At 38, she was a single mom of three working two jobs after her husband decided family life was “too restrictive for his spirit” (translation: he was a commitment-phobic man-child). She was convinced she’d crashed and burned. Five years later? Running her own bookkeeping business, dating a decent human being, and thanking the universe her ex took his “free spirit” elsewhere.

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A – Assess Your Assets (Yes, You Have Them)

[rolls up metaphorical sleeves]

Let’s inventory what you’ve got going for you:

  • You’re raising two human beings (master-level multitasking skills)
  • You’ve survived 36 years on this crazy planet (resilience)
  • You’re self-aware enough to assess your situation (emotional intelligence)
  • You’re reaching out for guidance (wisdom and humility)

That’s a foundation many would envy. The problem isn’t that you’ve failed—it’s that you’re using someone else’s measuring stick.

I – Identify New Directions

“Failure” isn’t a destination—it’s just a really unpleasant detour.

Here’s where I’m dead serious though: the worst thing you can do right now is nothing. Paralysis is the only true failure. Whether it’s education, career pivoting, building community, or reimagining your definition of family—movement in any positive direction changes everything.

Consider the unexpected comparison: Your life right now is like a startup that didn’t get its expected funding. Successful entrepreneurs don’t fold—they pivot, find new investors, or discover a more profitable market niche. Your personal “business model” needs adjustment, not abandonment.

L – Launch Imperfectly (Perfect is the Enemy)

[gestures emphatically with coffee mug]

“The gap between thinking about change and creating change is bridged only by the sketchy, wobbly footbridge of imperfect action.”

Truth bomb incoming (wrapped in a humor cushion so it doesn’t hurt too much): No one is coming to save you. The cavalry isn’t on its way. And that’s actually fantastic news because it means you get to be your own hero in this story.

Now, I know conventional wisdom says “make a five-year plan” and “build your emergency fund first,” but I think that’s overrated for someone in your position. Sometimes you need to light a fire under your life before carefully organizing the firewood. What’s your take?

We’ve all felt that crushing weight of thinking we’ve somehow failed the “life test” while everyone else passed with flying colors. What got me through it? Realizing that everyone’s taking a different test, and most people are faking their confidence anyway.

Your Second Act Starts Now

[stands up with dramatic flair]

At the end of the day, “failure” is just success taking an unexpected detour. Your GPS is recalculating, not permanently broken.

“Your children aren’t watching to see if you’re perfect—they’re watching to see if you’re resilient.”

Ready for your next move? Here’s your call to action: Take 30 minutes tonight, after the kids are asleep, and write your own eulogy—not the sad one based on your current outlook, but the inspiring one that could be true if you lived the next 50+ years with purpose and determination. What would you want it to say? That vision becomes your new North Star.

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[offers a high-five that morphs into a supportive shoulder squeeze]

Your homework assignment (and yes, I’m checking it): Find one person who reinvented themselves after 35 and reach out to them. Buy them coffee. Ask questions. Take notes. Steal their playbook shamelessly. They’ll be flattered, and you’ll be inspired.

What’s the wildest dream you’ve shelved because you thought it was too late? I’m dying to know, because I guarantee it’s not actually too late.

Think this advice is too simplistic for your complex situation? Challenge accepted—tell me why, and let’s problem-solve together. There’s wisdom in pushback.

Until next time, remember: failure isn’t a person, it’s just a crappy first draft—The Sage of Streetwise Wisdom!

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