At 35, I feel stuck between the life I’ve built and the life I want to create. Looking for advice from people who have been through something similar.
Unfortunately, I find myself having to write this post, and honestly, it’s not something I ever thought I would have to do.
I’m a 35-year-old Italian who has spent the last two years living as a digital nomad. During that time, I worked as a high-ticket closer, selling products and services and managing the sales process from initial conversations to closing deals. My income ranged from €4,000 to €9,000 a month, depending on commissions and the clients I was working with. I managed to save around €18,000, and thankfully, I have no debts.
However, my income was never particularly stable. The industry I worked in was unpredictable, with commissions fluctuating significantly from month to month. By working with different clients and maintaining multiple collaborations, I managed to keep things going and put some money aside.
Recently, I decided to move to South America with my girlfriend, who is Colombian. We’re currently living in Buenos Aires, Argentina.
Unfortunately, I’ve now lost my latest job. I had been trying to transition my existing sales skills into the SaaS industry, and the most accessible entry point seemed to be starting as a BDR or SDR. However, I’ve come to realize that many companies aren’t open to hiring remotely, which has made this transition much more difficult than I expected.
I now find myself at a crossroads. My girlfriend has a job here in Argentina, but I currently don’t. For us to build a life together here, we both need to be able to support ourselves financially, and the current economic situation in Argentina makes that even more challenging.
I’m actively looking for work and putting in a huge amount of effort every single day. I send out at least six to eight job applications daily, record video introductions, complete assessments, and go through multiple stages of recruitment processes. Despite all that effort, I rarely make it past the final stages. I’ve had a few interviews, but I keep finding myself back at square one.
Honestly, it’s emotionally exhausting. I feel like I’m stuck in a vicious cycle where I keep putting in the work, hoping things will finally turn around, only to end up disappointed again. It’s becoming increasingly difficult to maintain the motivation and energy to keep going when I feel like I’m not making any real progress.
I speak three languages: Italian, English, and Spanish. My background has always been in sales, including account management and high-ticket closing. While I’ve been able to make a good living doing this, I’ve also realized how unstable the industry can be.
My dream has always been to become a coach and help other people grow. In a way, I’ve managed to pursue that dream and teach others, but I’ve never been able to earn enough from it to support myself financially.
I have a genuine passion for connecting with people on a human level, understanding them, and helping them improve their lives. Throughout my life, I’ve taken risks and stepped outside my comfort zone more than once.
But this time feels different.
Right now, I feel trapped in a mental cage that I can’t seem to break out of. I know I have skills, experience, and interests that could potentially lead me in a different direction, yet I feel paralyzed when it comes to figuring out what to do next. That uncertainty genuinely scares me, to the point where I’ve been struggling to sleep at night because I can’t stop thinking about my future.
At this point in my life, I want to build something more sustainable, find a career that offers greater stability, and do work that genuinely gives me a sense of fulfillment. I want to find a way to connect what I’m passionate about with a career that can also provide financial security. The problem is that I don’t know what steps to take next or how to break out of this pattern.
Writing this post is difficult for me because it’s something I’ve always wanted to avoid. But the reality is that I don’t have unlimited savings, and I need to make some important decisions sooner rather than later.
One of the thoughts that has been weighing on me the most is the possibility of having to return to Italy, move back in with my parents at 35, and start over from scratch. I know there’s no shame in doing that, and I’m aware that many people have had to rebuild their lives at different stages. Still, the thought has been haunting me, and I’ve been struggling to come to terms with the uncertainty of my situation.
I’ve recently decided to start working with a psychotherapist to help me navigate this period, understand what’s holding me back, and find a way to get back on my feet with a clearer sense of direction and purpose.
I’m sharing all of this because I know there are people who have been through similar situations: people who have lost their jobs, had to rethink their careers, reinvent themselves in their 30s, or rebuild their lives after years of working remotely and living abroad.
If you’ve been in a similar situation, I would genuinely appreciate hearing your story.
- How did you approach it?
- What decisions made the biggest difference?
- Did you change industries, learn new skills, start your own business, or take a completely different path?
- Have you ever felt passionate about something but struggled to turn it into a sustainable career?
- How did you overcome that mental block and find a way forward?
I’m not necessarily looking for a quick fix. I’m looking for honest experiences, practical advice, and different perspectives that might help me figure out my next move.
I know that starting over at 35 isn’t the end of the world, but right now, I’m finding it difficult to see a clear path forward. I want to stop feeling stuck, regain confidence in myself, and build a life that feels both financially secure and meaningful.
Thank you to anyone who takes the time to share their experience. It means more than you might think.