In this episode, I sit down with real estate investor and coach Stephanie O’Brien to unpack her journey from getting licensed in 2006 to becoming a powerhouse in short sales, investing, and now coaching others through major transitions. Stephanie shares how the 2008 crash shaped her career, why she chose to specialize in solving tough problems, and how that path eventually led to her own personal and professional reinvention.

We dive deep into the mindset shifts required to go from chaos to clarity, how to recognize when you’re out of alignment, and why letting go of what no longer serves you is often the key to leveling up. If you’re feeling stuck or stretched thin, this conversation will help you realign and reset with purpose.

Episode Timeline:

[0:00] – Intro: how Stephanie got started in real estate pre-2008 crash

[1:02] – Why she leaned into short sales instead of running from the chaos

[2:21] – Building a business focused on helping people through hard transitions

[3:45] – The power of coaching and clarity during seasons of confusion

[5:17] – How to know when your goals are no longer in alignment

[6:29] – Breaking free from the “more is better” mentality

[7:38] – Getting honest about burnout and redirection

[8:50] – Stephanie’s own reinvention journey and what sparked it

[10:04] – From transactional real estate to transformational coaching

[11:16] – Creating margin in your life and business

[12:25] – Why entrepreneurship often reveals what we’ve ignored

[13:48] – Setting new standards and boundaries after burnout

[15:12] – Stephanie’s current coaching work and what lights her up

[16:03] – What alignment looks like—and how to find it again

[17:36] – Final words of encouragement for anyone stuck in the grind

5 Key Takeaways:

1. Realignment often starts with being honest about what’s not working.

2. Short sales and creative investing solve real problems for real people.

3. Burnout is a signpost—not a failure.

4. Your next level may require releasing what worked in a past season.

5. Coaching and community can create clarity faster than going it alone.

Links & Resources:

• Connect with Stephanie on Instagram: @the.real.stephanieobrien

• Coaching or speaking inquiries: Stephanie’s Website

• Join our free Facebook group for real estate investors: [Insert link]

• Learn more at JayAndAnnieAdkins.com

If this episode gave you the clarity or courage to pivot, rate and review The Real Estate Ride. And don’t forget to share it with someone who needs to hear they’re allowed to evolve.