We're taught that financial success and early retirement are the ultimate goals. But what happens when you achieve them and still feel empty? Why does having unlimited choices sometimes feel more paralyzing than liberating? Emma discovered that "doing too little can be just as draining as doing too much" - so what should we focus on instead?

👉 Find the full playlist of episodes HERE: https://www.youtube.com/playlist?list=PLO6l9CNQoSFdYrSofAAHBcTdsnpYk8iYg

Emma Steenson is a property investor, former management consultant, and executive coach who experienced "accidental early retirement" in her mid-30s after selling her successful business. Despite achieving financial independence and reaching what seemed like her finish line, she found that remaining idle without purpose was unsatisfying and draining. This led her to redefine success and train as a coach focused on helping SME founders and business owners who feel stuck or unfulfilled despite external success. Emma's work centers on helping leaders realign their goals with their own values to create meaningful momentum.

Today, expect to learn:

• The unexpected challenges of achieving financial independence too early and the existential vacuum it can create.
• Why "doing too little can be just as draining as doing too much" and what this means for our relationship with work and rest.
• How the paradox of choice makes unlimited options feel paralyzing rather than liberating, and what to do about it.
• The crucial difference between happiness (a fleeting emotion) and contentment (a deeper, more sustainable state).
• Why tunnel vision toward goals can be both helpful and harmful, and how to develop better discernment.
• How societal expectations and inherited models of success no longer fit our rapidly changing world.
• The role of coaching and reflective conversations in helping people clarify what they truly want beyond external expectations.
• Why letting go of finding "the one right answer" is essential for moving forward, even when it feels uncomfortable.
• Practical strategies for self-coaching and using trusted friends as thinking partners when professional coaching isn't accessible.
• How to redefine success through work-life integration, personal values alignment, and finding joy in daily moments rather than chasing abstract goals.
• And more!

Research shows that early retirement often requires restructuring life purpose, with many retirees experiencing the "retirement paradox" - dissatisfaction despite newfound freedom. The "paradox of choice" demonstrates how excessive options lead to anxiety and decision paralysis. Studies distinguish between momentary happiness and longer-term contentment, with contentment proving more sustainable. Executive coaching has been proven to improve self-efficacy and life satisfaction, while traditional linear career models are increasingly being replaced by flexible, multifaceted approaches to success.

W H A T T O D O N E X T :

GUEST LINKS ~

WEBSITE: https://emmasteenson.com

LINKEDIN: https://www.linkedin.com/in/emmasteenson/

HOST LINKS ~

WEBSITE: https://sevenjacobs.com

SUBSTACK: https://sevenjacobs.substack.com

SOCIALS: https://sevenjacobs.com/links

SHOW LINKS ~WEBSITE: https://sevenjacobs.com/lost-and-searching

YOUTUBE: https://www.youtube.com/@lostandsearchingpodcast

ALL EPISODES (Spotify): https://creators.spotify.com/pod/show/lostandsearching

ALL EPISODES (Apple): https://podcasts.apple.com/us/podcast/lost-and-searching/id1771369908

Shocka dives into the life-changing idea of choosing to be a “key” for others, instead of a “padlock”. Your daily choices and intentions can either unlock opportunities and inspiration, or lock possibility away. Through honest self-reflection and actionable advice, you’ll learn how vulnerability, personal responsibility, and living with purpose can empower you to create positive change for yourself and everyone around you.

Watch the full episode here: https://youtu.be/Q0vuhlPKx1E

Authenticity feels harder than ever when building something from scratch. We're told to "fake it till you make it," but what if that's actually holding us back? How do you lead with genuine confidence when everything feels uncertain?

👉 Find the full playlist of episodes HERE: https://www.youtube.com/playlist?list=PLO6l9CNQoSFdYrSofAAHBcTdsnpYk8iYg

Hattie Willis is the founder of GuessWorks, an entrepreneurship education company supporting thousands of founders and innovation teams across accelerators, universities, and multinational companies like DPD, Rambøll, and Lloyds Banking Group. She's also co-founder of IfWeRaise, a platform helping underestimated founders access knowledge and networks to raise capital on fairer terms, and hosts the podcast Not My First Guess. As a speaker at major events including Web Summit and Sifted Summit, Hattie advocates for human-centered leadership that embraces vulnerability and psychological safety while building innovation capability in uncertain times.

Today, expect to learn:

• Why charisma is actually competence meeting warmth, not just being impressive

• How to recognize "baby burnout" versus actual clinical burnout and what to do about each

• Why psychological safety is essential for innovation and risk-taking in teams

• The stark cultural differences between US, UK, and Nordic approaches to entrepreneurial failure

• How to move from work-life balance to work-life harmony and what that actually means

• Why soft skills become more critical as technical innovation cycles shorten

• How to overcome persistent imposter syndrome and reframe your credibility narrative

• What it means to build without a blueprint and embrace authentic leadership

• How to separate your internal narrative from reality when making decisions

• Why "I have to" versus "I get to" mindset shifts can transform your motivation... And more!

W H A T T O D O N E X T :

GUEST LINKS ~

LINKEDIN: https://www.linkedin.com/in/hattie-willis-2b47b376/

INSTAGRAM: https://www.instagram.com/notmyfirstguess/

WEBSITE: https://www.ifweraise.com

HOST LINKS ~

WEBSITE: https://sevenjacobs.com

SUBSTACK: https://sevenjacobs.substack.com

SOCIALS: https://sevenjacobs.com/links

SHOW LINKS ~

WEBSITE: https://sevenjacobs.com/lost-and-searching

YOUTUBE: https://www.youtube.com/@lostandsearchingpodcast

ALL EPISODES (Spotify): https://creators.spotify.com/pod/show/lostandsearching

ALL EPISODES (Apple): https://podcasts.apple.com/us/podcast/lost-and-searching/id1771369908

Sources & Jargon Buster:

• Psychological Safety: A team climate where individuals feel safe to take risks, make mistakes, and speak up without fear of negative consequences

• Work-Life Harmony: An approach that integrates work and personal life fluidly rather than strictly separating them

• Baby Burnout: Early-stage exhaustion and overwhelm that can be addressed with rest, distinct from clinical burnout

• Innovation Culture: Organizational environment that encourages experimentation, learning from failure, and adaptive thinking

• Founder Burnout: Chronic exhaustion specific to entrepreneurs facing uncertainty, financial pressure, and constant decision-making