Background:
I am a 30-year-old male with around 10 years of experience in SaaS sales, customer success, SaaS consulting/implementation, and product management/product leadership for a product studio. I’ve also dabbled in entrepreneurship, having pseudo-launched a micro-SaaS product and collaborated on various ventures, some of which faced challenges due to cultural clashes or unexciting business prospects. While I managed to save approximately $150k over the past 3-4 years, I invested it in businesses, incurred losses in the stock market, and, for the last 9 months, have been contemplating my next move. Currently, I have $50k left and am open to investing it for the right opportunity.
Challenges:

  • I am grappling with the difficulty of finding the right idea and following through with it, without succumbing to obstacles.
  • Confidence in myself and my chosen project is wavering, often tied to the nature of the idea I am pursuing.
  • There’s a fear of missing out on a conventional career path, such as becoming a product manager in a software company, which, despite being financially rewarding, feels unfulfilling due to my exposure to entrepreneurial environments. Job hunting is proving challenging due to the unconventional nature of my experience.

Personally, I bring to the table significant assets honed over the years. I thrive on being highly systematic—able to conjure up processes out of thin air using SaaS, Excel, Python, or whatever the situation demands. My knack for swiftly building trust and empathy is a standout feature, making me adept at navigating interpersonal connections. Financial literacy is a strong suit, as evidenced by my ability to forecast and work on P&Ls, leveraging unit economics to predict diverse growth scenarios and effort requirements.
I am self-driven, holding myself accountable and completing tasks with determination. Sure, dealing with ambiguity can be frustrating, but I’ve never been one to throw in the towel. I possess a versatile mindset, always open to learning and seeking advice when faced with challenges.
Yet, amidst these strengths, I keep circling back to the central issue: “What do I work on?”
Moreover, my mind has always been programmed to tackle something “impressive” – perhaps to satisfy some ego or insecurity acquired along the way. Ideas like AI or high finance initially captivate me, but I often hit a mental wall. The simplicity of basic, yet practical, concepts like a tuition service or prepped food delivery starts to appeal, even though others are already excelling in these areas. It seems I wasn’t built for a single role, leading me to the conclusion that building my own venture is the answer.
So, the real question I’m grappling with is:

  1. Is this current uncertainty, this Fear, Uncertainty, Doubt (FUD), a signal that I should opt for stable employment?
  2. Do others share these thought patterns, and if so, how have they navigated through them?

Any insight, personal experience, and maybe just a reality check would be greatly appreciated.

Thank you.