Sahil Bloom is the NYT Bestselling Author of The 5 Types of Wealth. On Friday, June 20, 2025, he posted this image on LinkedIn and a rather lengthy caption that hit me right in the solar plexus. His words carry the weight of hard truths lived, often in the shadows of entrepreneurship and capture so vividly the path I have walked myself. I felt compelled to share them with you here, because they deserve to travel far and wide, even if it’s just by hitching a ride on my Substack.
We are all beneficiaries of the sweat and tears of entrepreneurs whose names we may never know. If you find yourself in these words, take heart: not only are you not alone, but you are among the rare few who see the world from this vantage point—a view that grants us a depth of compassion and understanding that even fewer will ever come to know.
In this post, you’ll find Sahil’s original words followed by my own reflections and personal stories from my entrepreneurial journey. My hope is that in reading both, you’ll feel seen, understood, and maybe even a little less alone.
5 harsh truths nobody told you about entrepreneurship
1. Real freedom is terrifying.
Most people want the social media version of entrepreneurial freedom. In my experience, real entrepreneurial freedom looks…well…different.
Real freedom is terrifying.
It’s the recognition that everything is on you. It’s the acceptance that you have to hunt if you want to eat. It’s the accountability to recognize that when things aren’t going well, you are the only one who can change it. It’s staring out into the darkness. It’s riding the ups and downs.
Most people want the illusion of freedom. They wouldn’t last a few days with the reality.
But for those who accept the challenge, there is nothing more rewarding.
Cristy’s Comments:
Freedom comes at a great cost. For a long time, it cost me my sense of security and inner peace. Waking up each day knowing that not only is everything on you for you, but also on you for others who are depending on you—is a tremendously heavy weight to bear. At least for me.
Building my team as an entrepreneur has been like weight lifting: the heavier I lift, the more confident I become as a leader. I’ve stayed true to my heart-centered leadership philosophy of putting the team first. If you take care of your team, they’ll take care of you, your business, and your clients.
2. Most of society is built for traditional employment.
There are a lot of simple things that you take for granted as a traditional employee that disappear as an entrepreneur.
Like getting a mortgage to buy a house. The bank prefers a traditional (W2) employee making $100k per year to an entrepreneur making $250k per year.
The truth is that a lot of the societal infrastructure was built around traditional employment.
The point: Be prepared for headaches in unexpected places.
Cristy’s Comments:
Couldn’t agree more. Be prepared to manage your finances in unconventional ways. Talk to other business owners managing more money than you. Find CPAs who specialize in small businesses or work with many entrepreneurial clients, as they often know creative ways to guide you. Ask for help.
3. Lack of structure will be your worst enemy.
In my opinion, the single greatest challenge facing new entrepreneurs is the lack of this structure in their days.
It’s a weird feeling waking up and not knowing what you should be doing. It’s oddly disconcerting. And for those who’ve grown accustomed to the structure of the traditional path, it can be a significant blocker to progress.
Cristy’s Comments:
This was a hard lesson to learn. In the early years, I believed I was organized and on track; but in truth, I was stuck in survival mode. From 2015 to 2021, I was heavily reliant on marijuana as a coping mechanism. This is the first time I’m publicly sharing that I was quite the pothead at one time. It numbed the pressure and feelings, but it also severely clouded my clarity, sense of direction and overall execution when it came to achieving my goals.
Looking back at this photo, I see a woman whose business was growing fast. Faster than she knew how to handle. I had no roadmap for managing the pressure, the expectations, or the quiet but intense spotlight that came with my brand’s rising visibility in New Orleans.
I was high during this shoot. At the time, I was also using marijuana to dull the ache of insecurity and self-doubt. I didn’t feel confident enough to show up fully as myself, so I smoked to take the edge off—to survive the moments.
Behind this smile was loneliness. Fear. A deep resistance to being seen. I didn’t want to be the face of my company anymore because I felt inadequate. And I was terrified of the very visibility I had worked so hard to create.
I was constantly busy, spinning in circles, working in the business rather than on it. I felt isolated, constantly working behind a screen, and disconnected from genuine community. I was surrounded by people I thought had my best interests at heart, but didn’t. I spent most of my days reacting instead of intentionally leading. Even when I thought I was being proactive, I had no real direction. There was no one holding up a mirror to show me what I was doing well, or where I could grow. No mentor, no guidance, no professional support.
Then one day, I got fed up with feeling numb. And I decided I wanted to feel again. That decision marked the beginning of real change. So much so that a few months later I was asking my then-husband for a divorce, followed by moving to another state to find myself again.
Then the universe stepped in. Someone crossed my path and recommended a mentorship program. While it didn’t offer the clarity I initially hoped for, it led me to something far more impactful: my mentor, David.
Since we began working together in November 2023, both my life and business have taken a transformative leap forward. His mentorship has provided the structure, accountability, and community I had been missing. I wake up more grounded and confident, knowing I’m no longer carrying the weight alone.
David’s circle is filled with high performers, and people who have a fundamental understanding that entrepreneurship is not meant to be done in isolation. His support and guidance have been life-changing. As he often reminds me, he’s the kind of mentor who would “back me up in a bar fight”. And knowing that has made all the difference.
4. It’s a lonely journey (most of the time).
When you start living differently, you will stop fitting into your old environments.
The people you felt aligned with start to feel distant. It's almost as if you start speaking an entirely different language. You no longer have much to talk about. They don't seem to understand your values or motivations.
And as you leave behind the old, you have yet to attract the new.
The season of loneliness is natural—a sign you're on the right path. Embrace it. Use the solitude and the focus it unlocks to accelerate your growth.
Cristy’s Comments:
It truly is one of the loneliest journeys. Even with a partner or close support, no one feels what you feel as deeply as you do. But I’ve found that loneliness can be transformational.
In that quiet space, we meet our true selves. We discover our grit, passion, and determination. And yes—we meet the harsh inner critic, the shadow voice as I like to call it, who tells us we’ll never make it.
Here’s what I’ve learned: that shadow voice doesn’t need to be defeated. It needs to be loved. It needs to be embraced. When you shower it with compassion, you start to recognize the shadow voice in others too.
And that’s when transformation happens.
5. Nobody cares if you win (or if you lose).
A mentor gave me a simple piece of advice early in my journey: Nobody cares.
When you're winning, when everything is going well, when you're crushing it, nobody cares. When you're losing, when everything is falling flat, when you're down and out, nobody cares.
It doesn't mean nobody loves you. It just means nobody cares about your life as much as you do. It just means that you are in control.
It’s all on you. Nobody is coming to save you.
So you might as well do the thing. You might as well pursue what calls you. You might as well live your life on your own terms.
Cristy’s Comments:
He’s right. No one is coming to save you. But what I am not so sure about is the “nobody cares” part.
I can name several people who care, from my team, my mentor, my partner, my longtime loyal customers, members of my Cali Krewe Membership program, my family, etc. They do care.
But even if you “lose” you still won because you gave something your all, you took a risk to create something of your own, and you are so much better for it.
Remember, you are not alone.
My Final Thoughts
If you’ve been walking a similar path, perhaps spinning your wheels, feeling isolated, or just plain tired of pretending everything’s fine, I want you to know this: supported is nearby. We don’t talk enough about what it really takes to do this work and keep showing up.
Entrepreneurship is as much an inner journey as it is a business one. And sometimes, the bravest thing you can do is decide to feel deeply again with intention and take action from this place.
What I’ve learned is this: even the highest achievers, the ones who look like they have it all together, need support. Sometimes more than anyone else. The weight of leadership, responsibility, and visibility can be crushing without the right people in your corner. That’s what real entrepreneurial community is about. It’s not simply cheering each other on when we’re up, but holding space and offering real presence when we’re working through the hard parts too.
If this post resonates with you, I’d love to hear from you. Whether you're in a season of momentum or looking to find your footing, I’m here. Not only cheering you on, but holding space, and always happy to connect.
Let’s keep hiking mountains together.
With love,
Cristy
About The Author
Cristy Cali is a writer, award-winning entrepreneur, and globally recognized jewelry designer with roots in Guatemala and New Orleans. Cristy’s writing infuses positivity and authenticity into her candid lessons on personal growth & entrepreneurial success in building a 7-figure jewelry brand.
Follow Cristy on Instagram and TikTok for insights and stories!
Submit a membership request to Cristy’s Beloved Club on Facebook to stay connected.
Subscribe here for the latest jewelry news and offers.