How I Hit Rock Bottom, Quit Drinking, and Rebuilt My Life

Joan Westenberg
6 min readSep 9


I crawled to the bathroom, clutching my pounding head. As I hoisted myself up to the sink, I caught a glimpse of my bloodshot eyes in the mirror. I didn’t remember getting home from the bar last night. Or even leaving. Just flashes of downing shots and stumbling into a cab.

This was rock bottom.

I was at the top of the startup world just a few years ago. As marketing director for a promising tech startup, I helped drive our growth from scrappy underdog to multi-million dollar acquisition by one of Silicon Valley’s giants.

But the nonstop pressure and stress of startup life had driven me to drink alone every night to take the edge off. High-functioning and successful on the surface, I managed to hide my growing dependency from coworkers and our investors. But inside, I was losing control.

The truth stared back at me from the mirror that morning, still in my rumpled clothes from the night before. My partying lifestyle would eventually kill me if I didn’t do something to regain control. But how could I possibly break free at this point? I felt trapped, my body and mind held hostage.

A tiny voice inside said, “This is your last chance — take back your life before it’s lost forever.”

In that hungover fog, I knew I had to choose: either continue sliding deeper into the abyss or claw my way out towards the light. I chose life.

I started small but deliberate steps. I poured out every last drop of alcohol down the drain — over 7 liters of poison. I looked up AA meetings and made an appointment with a counselor specializing in addiction. I knew the road ahead would be long and difficult, filled with setbacks and tests of my resolve. But I decided to focus single-mindedly on sobriety, taking it one anxious day at a time.

Relearning healthy ways to manage stress, socialize, and relax without alcohol became my full-time job. I had to find meaning and reward in simple things — a good book, chatting with friends over coffee, and running. I embraced this second chance at life that I was fortunate to receive.

As I regained stability in recovery, I questioned whether I wanted to keep pursuing the demanding startup path that had fueled my addiction. The thrill of scaling a company had lost its luster. I felt burnt out, like a hamster on a wheel.

Was it time to regain control and build something for myself on my terms? The choice became clear — I knew I had to level up and leave the rollercoaster of startup life behind.

Right after our successful acquisition, I left the company on good terms. I wanted to pursue my side hustle of offering marketing consulting to startups full-time. During my recovery, I slowly built up my skills and client roster over nights and weekends.

Now fully sober for 6 months, I leaped into entrepreneurship. I launched a boutique digital marketing agency focused on the tech industry. I loved advising clients directly while controlling my workload and schedule. Being a solo founder was thrilling but daunting — learning sales, finance, and operations on the fly while charting my course without a boss or investors to please.

But I relished this newfound freedom and flexibility. Within 3 years, I had profitably grown my solo agency to support a thriving client roster. My new goal emerged: to build, spin out, enjoy, and sell 25 micro-companies as a solo founder in the next 48 months.

The sober me from the bathroom floor could never have envisioned this solo empire just a few years ago. But by facing my demons, I gained priceless resilience, perspective, and wisdom that drove my comeback.

Today, I’m a successful solo entrepreneur, mentor, and living proof that personal setbacks can become powerful launchpads. I made turning adversity into an advantage my superpower. And this is a skill anyone can develop, no matter how hopeless a situation feels.

To those staring into the void, seemingly suffocating in darkness — know that footholds exist if you search for them. Inch forward each day, however slowly. Ask others for help and guidance. You have more strength within you than you realize.

I’m living proof that deliberately choosing to change your circumstances is possible, even when it seems unlikely. My advice to anyone struggling is simple: never fully abandon your hope. Hitting rock bottom gave me this unshakeable core belief — the only real failure in life is giving up on your future potential for growth.

However far you’ve fallen, you can still turn things around and build the life you want. Believe in your innate ability to transform and elevate yourself. My greatest successes have come from my darkest days.

With this newfound purpose, I also felt called to help others battling the demons of addiction. I began sharing my story of recovery on my blog and social media. The feedback was humbling — so many people said my honesty and advice gave them hope.

I started volunteering at a local addiction treatment center, mentoring others through early sobriety. Helping fellow addicts reinforce their recovery filled me with meaning. I aim to open a nonprofit rehab facility to provide free treatment.

On my one-year sober anniversary, I reflected on how utterly my life had transformed. Not just externally but deep inside. I was calmer, more present, grateful for everyday moments. I cherished time with family and friends in a way I never had before. Past-me lived furiously chasing the next high — whether from alcohol or success.

Now, I live intentionally. My renewed energy is focused on my business, inner growth, helping others, and self-care. Ironically, my success accelerated even more once I stopped hustling so obsessively. It flowed naturally from my rebalanced priorities.

I know my disease will always lurk in the shadows, waiting for an opening. Vigilance is essential — I still talk on the sobriety Discord servers and work with my therapist and circle of believers. But I also celebrate how far I’ve come.

Recovery is not a linear journey. Sometimes, I still stray off the path — but I find my footing again quicker each time. Progress over perfection is my motto.

On my second sober birthday, I took a far different view. Gone was the shame and angst around my addiction. In its place was deep gratitude for overcoming that darkness and the lessons it taught me.

Without that crucible of hitting rock bottom, I would not be living the life I have today. I would not have found my calling to help fellow addicts and entrepreneurs. I would not have the profound sense of purpose that animates me.

My journey has shown me that we all have reservoirs of strength and wisdom deep within. It takes immense courage to face our inner demons — but doing so unlocks our greatest growth.

If you feel trapped in darkness, have hope. Take that first step, no matter how difficult. Reach out and peel back the layers keeping you from your highest self.

Freedom awaits on the other side. You have a beautiful life waiting to be created — if you walk towards it.

I’m rooting for you. We’re all in this together.

I’m Joan. Transgender. Solopreneur. Tech writer. Founded studio self, a marketing agency, community, & product lab.



Joan Westenberg

🍕 I write about tech + humans + economics.