RS391 - Wild and Wiser: Kelly Keating on portfolio working and designing a life with intention

From a senior corporate career to coaching, festivals, and a master's degree - Kelly Keating's story is about what happens when you stop letting life happen to you and start designing it deliberately. Anna Lundberg talks with the founder of Wild and Wiser about building a portfolio life after 40, navigating the financial realities of leaving a stable career, and why "enough" looks very different when your values are finally doing the driving.

Key takeaways:

• Success on your own terms takes time to define. Kelly's shift came not from burnout or crisis, but from a gradual deepening of self-awareness through coach training, parenthood, and a late ADHD diagnosis - all of which changed what she was willing to tolerate.
• The try-before-you-buy approach to leaving corporate. By building her coaching practice part-time over eight years while still employed, Kelly made the leap with far less financial and psychological risk than if she'd jumped cold.
• The financial case for leaving is often stronger than it looks. Most people never sit down and properly do the maths. Kelly found that stripping out the "emotional spending" that comes with an unfulfilling job made the numbers far more workable.
• Portfolio working is a season, not a system. Between coaching clients, associate work, a master's degree, and a festival she's launching, Kelly's week looks different to most - and that's entirely the point.
• Freedom and flexibility aren't the same thing. Kelly is arguably working more hours than ever, but the nature of those hours - the variety, the autonomy, the alignment with her values - is what makes the difference.

If Kelly's story has you thinking about your own next chapter, a good first step is a conversation. Book a free clarity call with Anna at onestepoutside.com/call.