What to do when you’re making good money but hate your life
… and how to design a life that doesn’t require an escape plan
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If You’re Thinking “I’m Successful But I Feel Trapped” – You’re Not Alone
If you’ve found this article, you’ve probably Googled phrases like ‘I hate my job but make good money.’ Maybe you searched ‘how to leave a successful career’ at 2 AM.
Maybe you’re sitting in your car after another draining day, wondering how you ended up feeling so stuck in a life that looks perfect from the outside.
Recently, I found myself re-listening to a recording from 2019 – a phone call with a psychic who had been referred to me by a friend.
This woman had accurately predicted my friend would have twins, so naturally, I was curious about what she might see for my own life.
As I sat with my handwritten notes from that conversation, I was struck by how much I heard this time around that I had completely missed when I was living it.
Sometimes we need the gift of hindsight to truly understand the wisdom we’ve been given – and to see how far we’ve actually come.
Why Smart People Stay Stuck in Jobs They’ve Outgrown
The guidance I received in 2019 was clear: Focus on your therapy practice first. Build a solid foundation before expanding into lifestyle design coaching work.
At the time, I was asking about my whole life – career, relationships, purpose – and receiving scattered advice from all directions.
Looking back, I’m grateful I took that strategic approach. I invested in a coaching program. It helped me build my therapy-focused website, aliveexplorations.com.
I learned about Google Ads, networking, and what it really meant to be a business owner – not just someone with a skill, but someone who could build something sustainable and meaningful.
This is where most people get stuck: they have the vision and the desire for change, but they lack a clear roadmap to design a life that honors both their values and their practical needs.
They stay in jobs they’ve outgrown because they don’t know how to bridge the gap between their current circumstances and the wholehearted life they truly want to create.
The Fear That Keeps High Achievers Paralyzed
Let me take you back to 2017, when I was facing the biggest career decision of my life.
I had what everyone would call a “great job” – good pay, beautiful location, meaningful work. When I was hired, the administrator said, “It’s nice to have such a free spirit here.” I was taken aback – I didn’t see myself that way.
But she was right. I’d spent years living in different states, taking solo road trips with my dog, and working at a wilderness therapy treatment center.
I was getting my first “big girl job,” and I was genuinely thrilled. I even did walk-and-talk therapy with clients down the lane when the weather was nice.
Yet something inside me was restless. I’d already explored whether my employers could accommodate a more flexible work environment, but this was before telehealth was widely accepted. I worked in a highly collaborative space where remote work would have been challenging.
The fear that keeps most high achievers paralyzed is this: What if I give up something good for something that might not work?
Eventually, the free spirit in me that she saw before I did was calling for my attention, so I decided to jump. I jumped alone and scraped together education and community along the way, instead of starting with clarity and mentorship.
People Tell Me: “I Invested in Coaching But Nothing Changed” – The $50K Learning Curve
After quitting my job, I made what felt like the biggest financial risk of my life: I put $10,000 on a credit card to enroll in a business coaching program.
There I learned to design a webinar sales funnel in eight weeks. I had no job to pay for it, but I felt the urgency to make it work.
Over the years, I’ve invested more than $50,000 in coaching and business education.
If you’re thinking “I’ve tried coaching before and it didn’t work,” I understand that frustration. The difference isn’t always the program. It’s about timing, your readiness to implement, and having the right support system.
Here’s what I learned about managing the financial risk: while debt isn’t ideal, by managing credit strategically, I’ve paid very little interest and maintained a credit score above 800. This financial stability became an important part of my lifestyle design strategy.
Meanwhile, I was going through the licensing process to become a Licensed Professional Counselor.
At the same time, I decided to sell my house (where I’d been living for the cost of utilities while my roommates paid the mortgage – an early example of creative lifestyle design!).
And yes, I sold it as my own realtor because I’ve always been determined to figure things out myself.
Looking back, I could have done all this faster, kept more money, and felt far less stress if I’d had a clearer roadmap.
I had notebooks full of dreams and was lucky to have education, skills, and faith – but I could have used more strategic structure.
How to Build Your Dream Life While Keeping the Lights On
Once I sold my house, I bought a semi-converted school bus. I spent a year turning it into my home office on wheels with help from my retired parents.
This wasn’t just about adventure – it was about proving that you can design a life that supports both your financial needs and your deepest values.
I’ve traveled the US in that bus. I’ve taken it on ferries to Pacific Northwest islands and crossed into Mexico and Canada.
Sometimes I park it and take international trips without neglecting my work.
This is what’s possible when you stop thinking in terms of either/or and start designing both/and solutions.
For years, I’ve been building a counseling practice while developing a coaching business. Proceeds from counseling go to fund the coaching work. I’m generating more revenue than ever while maintaining the lifestyle flexibility that matters most to me.
The key insight: you don’t have to choose between financial security and personal freedom. You can design systems that provide both, but it requires strategic thinking and patience with the building process.
Why “Follow Your Passion” Advice Fails (And What Works Instead)
The psychic was probably right – I would have reached financial stability faster by focusing solely on therapy. But here’s what the “pick one thing and stick with it” advice misses: some of us are builders by nature. We can’t help but tinker, create, and expand.
My lifestyle design coaching work is like the hot rod in my garage – I can’t leave it alone because the building process itself feeds my soul.
The mistake isn’t having multiple interests; it’s not having a strategic approach to managing them.
I think about other moments when I could have made different financial choices.
When I sold my house to finance my nomadic lifestyle, I considered a home equity loan instead. I could have kept the house and become a landlord, building a real estate portfolio.
At the time, things felt uncertain and I hadn’t developed my entrepreneurial confidence yet. I just needed my spirit to feel free again.
I wasn’t ready to juggle property management on top of all the other new developments in my life. The house went to a wonderful couple who contribute to that community, so it wasn’t a wrong decision – just a different path.
The Secret to Sustainable Success Without Burnout
Here’s what I’ve learned about achieving goals without burning out: I used to rush from one achievement to the next without pausing to appreciate what I’d built.
Now I make a point to love and enjoy today, even while taking consistent steps toward my bigger vision.
My counseling practice is intentionally designed to be manageable rather than overwhelming.
I’m integrating EMDR into my evolving practice, and I deliberately keep my caseload at a level where I can be fully present with each client. This isn’t about settling for less – it’s about designing for longevity and quality of life.
All we can do is check the rearview mirror, learn from our experiences, and keep moving forward with better information.
What It Really Looks Like to Design Your Ideal Life
Today, my vision is clear: Alive Explorations as a collaborative wellness center where online practitioners work together to enhance the holistic wellness of our clients.
In the vision, I see my counseling practice providing a stable foundation while my lifestyle design work helps people create lives they don’t need to escape from.
I aim to feel open and receptive to receiving abundance more easily.
I know that I’m providing genuine value that helps people live more authentic and balanced lives.
What I’ve built can grow sustainably, even though growth always brings unknowns that require courage to navigate.
Your Turn: How to Stop Postponing Your Dreams
If you’re reading this and thinking “this sounds like my story,” you might be someone who feels that internal calling for change. Not because you want to escape your current life, but because something inside you knows there’s more waiting to be created.
You might be successful but feel trapped by that success.
Perhaps you’re making good money but not living the life you truly want.
Some of you have notebooks full of dreams but need help creating a strategic plan to bring them to life.
You don’t have to figure it out alone, and you don’t have to take $10K leaps of faith without a safety net.
Ready to design a life that doesn’t need an escape plan?
Watch my free masterclass (link) where I’ll share the exact framework I wish I’d had during my own transition.
This is the strategic approach that could have saved me years of trial and error and helped me build sustainable success more efficiently.
Or if you’re ready to dive deeper, explore Lifestyle Design Mastery (link) and join a community of people who are creating authentic, integrated lives with a proven roadmap, ongoing support, and guidance from someone who’s already navigated this journey.
The road ahead may be uncertain, but it doesn’t have to be traveled alone.
What part of you is calling for change? And what would become possible if you finally listened?
