Tim Timmons and I go back about thirty years. He played at my wedding. He worked alongside my dad, Stan, for years, and somewhere in all of that he became one of those friends who changes how you look at your own life. Twenty-five years ago he was told he had five years to live. Stage four, incurable, tumors that are still on his liver today. He is still here, he is still writing, and he will tell you plainly that he is not celebrating cancer. He is celebrating the perspective it handed him.

What we ended up talking about is the space in between. Tim has a rule for it. He is trying to use more words that end in I-N-G than words that end in E-D. Not "I learned this," but "I am learning." Not "I figured it out," but "I am figuring." Not healed, but healing. That one small change is the whole posture of his life, and you can see it in the biggest calls he has made. Walking away from a church job he held for fifteen years. Funding a record on Kickstarter with no safety net. And then deciding he would never open a door for himself again. No schmoozing. No pushing his way into rooms. He has kept that for fifteen years, and in that time he has signed record deals, co-written a Grammy nominated song, and watched Milo Ventimiglia play him in a movie.

He also talks about the failure, and he does not soften it. A church called The Following that he and a friend built and then talked themselves right out of, until forty people were meeting in an Orange County motel alongside the people who lived there. It fell apart. He calls it the greatest failure of his life and the three years he grew the most. His new song Between is out now, and he says it is the most personal one he has written. If you are sitting in your own in between right now, waiting on an outcome you cannot control, this hour is for you.

In this episode:

• The grammar rule he lives by: more words ending in I-N-G than E-D
• Quitting a fifteen-year church job, and why he says working for God sucked the life out of him
• The Kickstarter that no label wanted, until every label wanted it
• Five years to live, twenty-five years ago, and what that does to how you spend a Tuesday
• The experiment he has run for fifteen years: never open a door for yourself again
• Surrendering the outcome, and why he had to stop being the CEO of everything
• The Following: the church that failed, and the three years he grew the most
• Why the biblical word for hope has almost nothing to do with outcomes
• Watching Milo Ventimiglia play his hardest moments, and finding compassion for himself
• Why we are so good at moving past grief and so bad at actually grieving
• The X he writes on the underside of his wrist every single morning
• Cancer is the dumbest. The perspective is the gift.

More from Tim:

His new song "Between" is out now: https://al.ffm.to/between.MXO

His book, Waking Up Again, is out now in hardcover and on Amazon.

timtimmonsmusic.com

Instagram and TikTok: @timmonsmusic

The 10,000 Minutes Podcast and the 10,000 Minutes nonprofit: @10kminutes

I Can Only Imagine 2, with Milo Ventimiglia playing Tim.

Work with Sara: https://saraemmersoncoaching.com. If you are standing in the middle of something and you want someone in the messy middle with you, book a coaching consultation.

If this one lands, follow the show and send it to the person you thought of while listening.

Annie Aiello grew up the youngest of six in a Chicago Italian family where the currency was academics and athletics, and the artist in her got quietly shushed. So she took the safe route. Business degree. Art minor, because that was allowed. Ad agency. Then an MBA, because she wanted something with more meaning in it than a widget.

Twenty-three years into a marriage she had promised herself she would never leave, she left it. She walked out of ministry into a corporate job that doubled her salary and made her miserable, and found herself a single mother trying to get two teenagers to college.

What she built out of that is Always Olivia, a national Olivia Newton-John tribute show. She started it because she needed joy and she needed money and she had exactly one skill nobody could take from her. She funded part of it with the proceeds from the house she had to sell.

This episode is about the mechanics of that. How she found the people who already knew how to do what she needed to do. Why the wigs, of all things, were the place she almost quit. What it took to walk out on a stage in a 1970s wig with her whole family in the audience, certain she was about to be laughed at. And what it costs to become a beginner again in public, twice, once on a stage and once, at fifty-something, back in the dating world.

Annie Aiello. Mother. Creative Voice. Singer. Songwriter, Lead singer of "Always Olivia," the Ultimate Olivia Newton-John Tribute, Producer, Child of God.

In this episode:

- Why "desperation breeds creativity" is not a consolation prize, it is a method

- The rule she runs her life on: when you do not know how to do something, go learn it from the people who do

- Flying to Vegas to meet a Cher tribute artist, Bob Mackie's understudy, and the woman who costumed Olivia at the Flamingo

- Choosing to put the house money into the show instead of into retirement, and finding an investor for the rest

- The wig that nearly ended it before the first show

- Standing backstage thinking "I am going to be so interpreted as a joke," and walking out anyway

- Giving a portion of every show's proceeds to the Olivia Newton-John Cancer Wellness and Research Centre, after losing both parents to cancer

- Throwing out perfectionism when you lead a band, because every crowd is different

- Being a beginner again at fifty-something, on stage and in the dating world

Sara's frame that runs underneath the whole hour: we only do things if we want it enough or we need it enough, and the best intersection is when both are present.

More from Annie:

alwaysoliviatribute.com

annieaiello.com

Instagram: @alwaysoliviatribute and @therealannieaiello

Catch the show live: Taste of Melrose Park in September, Australia in October for the Wellness Walk, then Florida and North Carolina in November.

Work with Sara: https://saraemmersoncoaching.com. If you are standing at a crossroads and you want someone to sit in the messy middle with you, book a coaching consultation.

If this one lands, follow the show and share it with the person you thought of while listening.

Emily Bache and Abigail Breslin have been best friends since they were eleven, grew up sharing one closet, and never actually chose their own name. A street photographer shouted "there's those WanderLust Girls" at them on a sidewalk, and it stuck. Fifteen New York Fashion Weeks later, they've styled for Playboy, Macklemore, Bloomingdale's, Jack White, and Major League Soccer.

In this conversation they tell Sara how a college blog started because one of them owned all the tops and the other owned all the pants, how they cold-emailed their way into 65 shows at their first Fashion Week with no credentials and nobody to vouch for them, and how a client's offhand comment sent them across the street into a bank to ask a stranger how you start a company. They also talk about the lunch invitation they almost turned down that became a Playboy job, the day they showed up in thigh-high boots and boas to what turned out to be bootcamp, and the SNL emergency that proved who was actually in their corner.

The thread running through all of it: every time someone advised them to tone it down and look more normal, it cost them. They tried it once, wore blue jeans, and watched followers leave. The thing that makes you weird is usually the thing people came for.

In this episode:

• Why the weird invitation is usually the one holding the door open

• How to ask for something bigger than you think you're allowed to

• What happens when you tone yourself down to be more marketable

• Why you don't have to feel ready, you just have to ask the embarrassing question

• How being wrong alongside someone makes risk survivable

• Why a $100 job is still a relationship, and how small gigs come back years later

Follow Emily and Abigail at @wanderlustgirls and thewanderlustgirls.com.

Ready for your own next step? Visit saraemmersoncoaching.com and book a coaching consultation.

Interior designer Johanna Lyle didn't start in design. She went from theater performer to video producer before a COVID-era reinvention turned a paint-splattered DIY Instagram into a six-figure design business. In this episode she tells Sara how she took a humbling pay cut to learn the craft, launched her own firm during a cross-country move with a husband about to hit zero income, and ran a Chicago clientele from Boston because that's what actually worked. She gets honest about the client she had to walk away from, the gut feeling she ignored, and why saying no is sometimes the bravest thing a business owner can do. It's a story about being willing to go backward to go forward, and trusting yourself when the timing is never right. Named a "Next Wave Designer" by House Beautiful, Johanna proves the greatest opportunities usually start with something that sounds risky. Follow Johanna: joelyleandco.com and @jo.lyle.design. Work with Sara: https://saraemmersoncoaching.com

What if resilience isn't just about mindset — what if it's rooted in your biology? This week Sara sits down with Jessica Maren: speaker, writer, and resilience educator who blends science-backed strategy with honest storytelling to help people stop spiraling and recover from setbacks. In this conversation: why your brain goes looking for a problem when life is finally calm, how chronic stress quietly rewires you to scan for the next fire, why failure feels so personal (and what to do about it), the difference between bouncing back and bouncing forward, and how a former elite athlete learned to regulate her nervous system on the biggest stages — including the private ones at home. Practical, refreshing, and a little bit science class. Follow Jessica @jessica.maren. Ready for your own next step? Visit saraemmersoncoaching.com and book a coaching consultation.

This week the guest chair belongs to the person who taught Sara to take risks in the first place: her dad. Stan Endicott is a musician and producer who spent decades making records in Los Angeles, the co-founder of Slingshot Group (one of the country's top coaching and staffing teams), an author, and the creator of the IMPROVLeadership model.

In this conversation: why we stop taking risks as we grow up and how to get the playfulness back, why grit can be terrible advice, the truth about the 10,000-hour rule, the one question to ask your boss instead of asking for a raise, the day he moved across the country with no job waiting, and the time he became one of the first outsiders to hear "I Wanna Dance with Somebody" before the world did.

Warm, funny, and full of the kind of wisdom you only get from a life of saying yes.

Learn more about Stan's work at slingshotgroup.org. Ready for your own next step? Visit saraemmersoncoaching.com and book a coaching consultation.

Sara's own coach of six years takes the guest chair. Amy Donovan, MCC, one of the first 150 coaches in the world, co-founder of PRIME Coaching Academy, and co-author of Who's the Boss?, has spent 25+ years coaching leaders through the decisions that scare them. In this conversation: the $5.5 million collapse that cost her nearly everything and the walk in the woods that started the rebuild, why courage always comes before confidence, how to borrow belief when yours runs out, the regret people actually carry at the end of their lives, and the t-shirt Amy had made that says it all: just say yes to the whole catastrophe. If you are standing at a crossroads, a part of you has already decided. This episode is about trusting it. Learn more about Amy at primecoachingacademy.com. Ready for your own next step? Visit saraemmersoncoaching.com and book a coaching consultation.

Gareth Pon said yes to climbing Mount Kilimanjaro before he Googled what it actually was. That one naive yes turned out to be the blueprint for his whole life.

In this episode of That Sounds Risky, Sara Emmerson sits down with Gareth Pon, an award-winning photographer, filmmaker, and creative director who pioneered Instagram in South Africa, moved across the world on the strength of a single social-media message, and now leads social-first creative for some of the biggest brands on the planet. His path was never a straight line. It was a string of small, slightly terrifying yeses that compounded into a remarkable career and an even more remarkable life.

Gareth and Sara talk about why risk is a muscle you build one rep at a time, why comfort is the killer of creativity, and why everyone needs one ridiculous dream. His is going to space, which is why there is a hidden rocket in every photo he posts. It is an honest, funny, faith-filled conversation about betting on yourself before you feel ready.

In this episode you'll learn:

• Why saying yes before you feel ready is how brave people actually build a life
• How small risks train the muscle that makes the big leaps feel possible
• Why comfort kills creativity, and how to keep reinventing yourself
• How relationships and generosity, not talent alone, open the biggest doors
• Why you need one ridiculous dream, and what happens the moment you believe it could come true
• How faith and letting go of control can free you to take bigger risks

"You need to have a ridiculous dream, because the moment you believe that dream can come true, everything else in your life becomes possible."

Follow Gareth's work (and hunt for the hidden rocket) at @garethpon.

Sara Emmerson is a certified life, business, and executive coach (ICF PCC) who helps capable people stop overthinking and make the brave move they've been putting off. Learn more and work with Sara at saraemmersoncoaching.com. New episodes weekly, so follow along.

Most people who feel stuck don't have a strategy problem. They have a belief problem. In this episode of That Sounds Risky, life and executive coach Sara Emmerson answers the questions she was asked as a guest on another show, and the answers turn into a masterclass on leadership, mindset, sales, and doing the scary thing anyway.

Fresh off a podcast interview with a host in London, Sara brings the best questions back to her own listeners: What does leadership actually mean? How important is mindset in success? What does sales really mean? Who does she coach, and why does this podcast exist at all? Her answers hold whether you're an executive, a business owner, an entrepreneur, or a creative who knows you're capable of more.

In this episode you'll learn:

• Why leadership is creating clarity in uncertainty, and why it starts with leading yourself first
• The difference between a strategy problem and a belief problem, and which one is actually keeping you stuck
• Why confidence doesn't come before action, it comes from taking action
• How fear, self-doubt, perfectionism, and other people's opinions keep high performers plateaued
• Why sales is service: helping someone see the gap between where they are and where they want to be
• The two kinds of regret, and why "I wish I'd tried" is the one you can't fix

Fear rarely shows up looking like fear. It shows up sounding reasonable. "I just need more time." "I need more clarity first." "Now's not the right season." If you've been saying the same line for months, this episode is for you.

In Episode 2 of That Sounds Risky, Sara Emmerson breaks down how to tell a real reason from a fear wearing a disguise, and what changes once you can see it. She walks through the RISK test, a simple way to check whether the thing you keep saying is information or fear: Repeated (how long have you been saying it?), Isolate (what's the fear underneath?), Sacrifice (what's it costing you to wait?), Keep moving (one small action in the next 24 hours).

She also makes the case that staying stuck is its own kind of work, that readiness was never a feeling you wait for, and that confidence shows up after you move, not before.

In this episode:

1. How to tell a real reason from an excuse (the RISK test)
2. Why "I need more clarity" is often a courage problem, not a clarity problem
3. The hidden cost of staying exactly where you are
4. Why every version of your life requires work, so choose the work that's worth it
5. How to take the next brave step before you feel ready

"Readiness isn't a feeling. It's a decision."

Sara Emmerson is a certified life, business, and executive coach (ICF PCC) who helps capable people stop overthinking and make the brave move they've been putting off.

Learn more and work with Sara at saraemmersoncoaching.com. New episodes weekly, so follow along.