E13: The Three Stages of Founder Loneliness (And Why Stage Two Almost Broke Me)

Founder Reality

Three years ago I was so desperate I asked a successful founder friend for a job. He said no - and saved my entrepreneurial career. Here's why the loneliness stage almost broke me and how I got through it.

The brutal reality of choosing a different path:

• While friends got $60K-120K jobs with benefits, I was making what they earned in 1-2 months
• Dating became weird - explaining you're "building something" at 22 sounds like unemployment with delusions
• When people at parties asked what I do, I'd freeze before explaining a business that wasn't making money yet
• Co-founders left for steady paychecks while I questioned everything

The three psychological stages every solo founder goes through:
Stage 1: Excitement (6-8 months)

• Felt like Neo in The Matrix - could see what others couldn't
• Every idea had potential, every late night felt productive
• Making early revenue while friends complained about assignments
• Choosing freedom while everyone else chose security

Stage 2: Self-Doubt and Isolation (3-4+ years)

• Friends graduated to real jobs, steady paychecks, clear career progression
• Social isolation hits hardest - you're the outlier still figuring things out
• My lowest point: asking that successful founder for a job in 2022
• Parents encouraging me to get employment
• The loneliness isn't just being alone - it's doubting you made the wrong choice

Stage 3: Self-Acceptance

• Not a magical date - it's about being in full agreement with your path
• Understanding you control your own destiny completely
• When friends complain about jobs now, I feel grateful I chose differently
• The loneliness is gone because I'm not lonely - I'm independent
• People respect and even envy the confidence in your choices

What shifted me out of Stage 2:

• Started taking care of myself - sleep, workouts, food tracking
• Stopped comparing myself to friends and co-founders
• Being true to myself instead of trying to be everything while being nothing
• Realizing I'm not built to be a good employee (tried internships, didn't work)

Key insights for each stage:

• Stage 1: Enjoy it, but Stage 2 is coming
• Stage 2: This is temporary but you have to do the work - take care of health, find your people
• Stage 3: Full agreement with yourself, no more seeking validation

Red flags you're in the brutal stage: Freezing when people ask what you do, feeling envious of friends' steady paychecks, questioning if you made the wrong choice, social isolation affecting dating and friendships.

Bottom line: The path of building something unconventional is lonely by design. But that loneliness teaches you things about yourself you cannot learn any other way. Your finances have nothing to do with these psychological stages - it's all about self-acceptance and controlling your own destiny.

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