The Anxious Achiever

What happens when the strategies that always worked for you suddenly stop working? How do you keep believing in yourself when success no longer feels certain? In this episode, I sit down with entrepreneur and author Jenny Blake to talk about financial uncertainty, career setbacks, and the emotional toll of building a business. Jenny shares what it was like to lose major clients, question long-held beliefs about success, navigate the "flop era" of entrepreneurship, and find new meaning through creativity instead of certainty. Tune in to discover how to navigate uncertainty with more self-compassion, patience, and purpose.

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In this Episode, You Will Learn

00:00 Why everyone looks rich on the internet, even when they're not.

04:15 What if your career doesn't go according to plan?

09:15 How Jenny Blake built a successful business after leaving Google.

13:15 What happens when your biggest source of income suddenly disappears?

18:45 How do you recover after a major career setback?

20:45 How to separate your self-worth from your achievements.

24:15 Can your body tell you when you're on the wrong path?

28:45 What Bell's palsy taught Jenny about burnout and self-care.

31:00 How atypical achievers can build careers that work for them.

35:15 How permission slips can help you navigate difficult seasons.

40:45 Would you still do it if it failed?

44:00 Is it okay if your greatest success is already behind you?

47:30 Why letting go of your old identity helps you move forward.

52:00 What permission do you need to give yourself right now?

Resources + Links

Learn more about Jenny Blake HERE

Get your copy of Jenny's book, Pivot HERE

Get your copy of Jenny's book, Free Time HERE

Get a copy of my book - The Anxious Achiever

Watch the podcast on YouTube

Find more resources on our website morraam.com

Follow

Follow me: on LinkedIn @morraaronsmele + Instagram @morraam

Follow Jenny: on LinkedIn @jennyblake

Which conversations have you been avoiding at work? In this classic episode, I sit down with Death, Sex & Money host Anna Sale to talk about why conversations about money, mental health, and personal struggles still feel so difficult in many workplaces. We discuss the shame that often shapes our financial decisions, how your upbringing influences the way you negotiate and advocate for yourself, and what to consider before telling your boss you're struggling. Anna also shares advice for setting boundaries, asking for what you need, and creating more honest relationships at work. Get ready to rethink the conversations that could change your work and your life.

Check out our sponsors:

Shopify - Sign up for a $1 per month trial, just go to shopify.com/anxiousachiever

Chime - Head to chime.com/achiever to sign up

Monarch - Use code ACHIEVER at monarch.com to get 50% off your first year

Physician’s Choice - Use code PCPODCAST10 at physicianschoice.com to get 10% off your entire order

Whatnot - Get free shipping on your first order. Just search W-H-A-T-N-O-T in the app store and start scoring amazing deals

Pebl - Take advantage of Pebl’s limited-time offer before it’s gone. Visit hipebl.ai today.

In this Episode, You Will Learn

00:00 The value of talking about hard things.

05:30 Which conversations are still taboo at work?

08:15 The shame that shapes our relationship with money.

12:15 Anna's experience with money anxiety.

15:45 The money mindset behind anxious achievers.

18:00 How do you negotiate without losing yourself?

20:30 How to set boundaries without apologizing.

22:45 A test before saying yes.

23:45 Negotiation advice for the start of your career.

27:30 Should you tell your boss you're struggling?

31:45 Choosing your wellbeing over your paycheck.

Resources + Links

Learn more about Anna Sale HERE

Get a copy of Anna’s book Let's Talk About Hard Things HERE

Listen to Death, Sex & Money HERE

Get a copy of my book - The Anxious Achiever

Watch the podcast on YouTube

Find more resources on our website morraam.com

Follow

Follow me: on LinkedIn @morraaronsmele + Instagram @morraam

Follow Anna: on LinkedIn @annasale + Instagram @annasalepics

Would you take four months away from work? Have you ever wondered who you'd be without your job for a while? In this episode, I sit down with Harvard Business School lecturer and The Sabbatical Project founder Dennis “DJ” DiDonna to talk about why many of us keep pushing until burnout forces us to stop, how intentional time away creates space to reflect on what really matters, and why rest isn't about doing nothing. DJ also shares ways to plan a sabbatical, navigate the uncertainty that comes with slowing down, and return with a stronger sense of purpose. Get ready to rethink time off as an investment in the life and career you want to build.

Check out our sponsors:

Shopify - Sign up for a $1 per month trial, just go to shopify.com/anxiousachiever

Chime - Head to chime.com/achiever to sign up

Monarch - Use code ACHIEVER at monarch.com to get 50% off your first year

Physician’s Choice - Use code PCPODCAST10 at physicianschoice.com to get 10% off your entire order

Whatnot - Get free shipping on your first order. Just search W-H-A-T-N-O-T in the app store and start scoring amazing deals

Pebl - Take advantage of Pebl’s limited-time offer before it’s gone. Visit hipebl.ai today.

In this Episode, You Will Learn

00:00 A new way to think about time away from work.

05:30 How sabbaticals create space for renewal instead of escape.

07:15 What is a sabbatical?

10:00 How burnout led DJ to rethink the life he was building.

15:00 Why achievement often comes at the expense of the people who matter most.

21:45 What are the benefits of stepping away from work?

26:45 When is the perfect time for a sabbatical?

32:15 What are the 3 types of sabbatical takers?

36:00 Why reconnecting with your craft can restore creativity.

41:00 How do you give yourself permission?

46:00 Are sabbaticals always relaxing?

49:00 How stepping away from work can make you a better leader.

53:00 Why taking time off is an investment, not an escape.

57:30 DJ's advice for planning your first sabbatical.

Resources + Links

Learn more about DJ DiDonna HERE

Pre-order a copy of DJ DiDonna’s book Big Time Off HERE

Learn more about The Sabbatical Project HERE

Get a copy of my book - The Anxious Achiever

Watch the podcast on YouTube

Find more resources on our website morraam.com

Follow

Follow me: on LinkedIn @morraaronsmele + Instagram @morraam

Follow DJ DiDonna on LinkedIn: @djdidonna

Could the way you think about money have more to do with your childhood than your bank account? In this episode, I sit down with personal finance expert Shannah Game to talk about why your relationship with money is often shaped long before you earn your first paycheck. We dive deep into money trauma, the stories we attach to spending and saving, and how those patterns influence our careers, relationships, and sense of self. Shannah also shares ways to respond differently to financial triggers and build healthier habits that align with the life you want. Get ready to rethink your relationship with money.

Check out our sponsors:

Shopify - Sign up for a $1 per month trial, just go to shopify.com/anxiousachiever

Chime - Head to chime.com/achiever to sign up

Monarch - Use code ACHIEVER at monarch.com to get 50% off your first year

Physician’s Choice - Use code PCPODCAST10 at physicianschoice.com to get 10% off your entire order

Whatnot - Get free shipping on your first order. Just search W-H-A-T-N-O-T in the app store and start scoring amazing deals

Pebl - Take advantage of Pebl’s limited-time offer before it’s gone. Visit hipebl.ai today.

In this Episode, You Will Learn

00:00 How childhood experiences shape your money habits and beliefs.

05:00 Why money is about so much more than dollars and cents.

07:15 How your money story influences your work and relationships.

12:00 A question that helps uncover your beliefs about money.

16:15 What is money trauma?

19:15 How to recognize your financial triggers before they take over.

22:00 How to interrupt unhealthy money habits with healthier thought patterns.

24:45 An exercise for changing your emotional response to money.

26:15 How do you build systems that reduce financial anxiety?

28:30 Why creating a regular "money date" builds confidence instead of fear.

30:00 What is financial self-actualization?

33:00 The 100-day challenge that helps you rethink every financial decision.

Resources + Links

Learn more about Shannah Game HERE

Get a copy of Shannah’s book Unraveling Your Relationship with Money HERE

Get a copy of my book - The Anxious Achiever

Watch the podcast on YouTube 

Find more resources on our website morraam.com

Follow

Follow me: on LinkedIn @morraaronsmele + Instagram @morraam

Follow Shannah on Instagram: @shannahgame

How do you lead when the future refuses to give you certainty? In this episode, I sit down with leadership experts Scott D. Anthony, Lisa Kay Solomon, and Chris Shipley to talk about what leadership looks like when uncertainty becomes the norm. We dive into making decisions without having all the answers, why leaders need to let go of the illusion of certainty, and how curiosity, agency, and even play can help teams adapt to change. We also share ways to navigate uncertainty, manage anxiety, and create workplaces where people feel empowered to do their best work. Tune in to discover why the future belongs to leaders who are willing to learn, adapt, and grow.

Check out our sponsors:

Shopify - Sign up for a $1 per month trial, just go to shopify.com/anxiousachiever

Chime - Head to chime.com/achiever to sign up

Monarch - Use code ACHIEVER at monarch.com to get 50% off your first year

Physician’s Choice - Use code PCPODCAST10 at physicianschoice.com to get 10% off your entire order

Whatnot - Get free shipping on your first order. Just search W-H-A-T-N-O-T in the app store and start scoring amazing deals

Pebl - Take advantage of Pebl’s limited-time offer before it’s gone. Visit hipebl.ai today.

In this Episode, You Will Learn

00:00 Why today's leaders need clarity instead of certainty.

03:15 What effective leadership looks like in an era of constant disruption.

08:15 Why clarity matters more than having all the answers.

11:00 Why learning often requires unlearning first.

12:45 How can you become more comfortable with uncertainty?

20:00 How mindfulness helps leaders stay grounded under pressure.

22:00 Why is agency one of the most important leadership skills today?

30:00 Why anxiety often leads people to avoid the work that matters most.

32:30 How to build psychological safety when everything feels uncertain.

39:00 How to create more joy, connection, and creativity at work.

44:45 Why appreciation and gratitude are essential for a thriving team.

53:45 Who are you when you take your job title away?

Resources + Links

Get your copy of Leading for Tomorrow HERE

Get a copy of my book - The Anxious Achiever

Watch the podcast on YouTube 

Find more resources on our website morraam.com

Follow

Follow me: on LinkedIn @morraaronsmele + Instagram @morraam

Follow Scott on LinkedIn: @scottdanthony

Follow Lisa on LinkedIn: @lisakaysolomon

Follow Chris on LinkedIn: @cshipley9