Some Regrets, Recollections, And Reminiscences From Years Of Full-Time Employment
This month one year ago, I quit my full-time job. Here are some regrets, recollections, and reminiscences.
I worked as a Staff Product Manager at Twilio till March 2022. Since then, I went on a sabbatical, launched a PM job hunt coaching service, and consulted a few businesses as a product (marketing) consultant.
Thanks to someone, this post reached the frontpage on Hackernews. This post received the most views, but also many polarizing views.
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Reasons I might fail: Premortem Of My Career Direction: Lessons From Poker And ‘Thinking In Bets’
Thumbnail credits to Image by storyset on Freepik, Image by pch.vector on Freepik, and Image by Freepik
What do I miss the most about working full-time?
1 - Regular discussions with a small group of people (colleagues). Meeting colleagues across days and weeks helped build great relationships, even when the meetings were virtual. I learned from The Happiness Hypothesis that these friendships bring me happiness. One-on-ones, scrum meetings, or project discussions were opportunities to continue building relationships.
2 - A physical place to work together or imagine myself working together. When I met someone virtually, I remembered times we’d met in person. Or I imagined meeting them sometime. I might reminisce about working in a meeting room, lunchtime in the cafeteria, or strolling between Cisco buildings. In-person time was fun (not the commute).
3 - I got quicker feedback cycles in full-time work. Brainstorming, mentoring, and presenting my work helped me get feedback. I usually got feedback within a week or a month if I’m working (hard) but in the wrong direction.
4 - As an employee, I did not need to pursue every single direction. Narrowing the scope allowed for deeper thinking and execution in one area. Anytime I identified new customer problems to solve, I would make a note. I would keep my priorities in mind and not jump on solving a new find immediately.
5 - I was not responsible for completing administrative, HR, recruiting, legal, finance, or tax tasks. Some had a drag-and-drop interface, such as expense reimbursement. Some had concierge, like travel booking. The rest did not occupy my mind, like writing employment contracts or privacy policies.
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What remained the same across full-time and an entrepreneur?
1 - Work didn't stop on weekdays. As a Staff Product Manager or an entrepreneur, my work didn't end at 6pm on Fridays. I would find pockets of time on weekends to think over important but not urgent problems. Both roles gave me empowerment and ownership, which drove me to work nights and weekends. I often (but not always) found that energizing.
2 - Family time didn't disappear. I had heard stories of entrepreneurs losing connection with their families. I also wanted to go all-in to grow my business. But, I choose not to go away from clean eating, working out, or spending time with my family. Those take up significant time daily, but I was able to maintain some balance as an entrepreneur.
3 - Execution took precedence over strategy or long-term thinking. Have you heard employees complain about working in the weeds? Have you heard complaints of not having time to think strategically and long-term? Those can go on a "career bingo". But, they were also true when I was a business owner. The buck stopped at me. But, it was hard to dissociate execution tasks from long-term thinking.
4 - As a Product Manager in a growth-stage company, I couldn't find time to write my thoughts in my newsletter or blog. I thought I could focus on this when I controlled my own time. But writing continues to be complicated. In fact, my backlog has swollen for 3 reasons.
a) I developed the skill of finding new ideas.
b) I had new professional experiences. And
c) I took away time from writing to experiment with delegating the writing.
What changed for the better?
I’ve covered my sabbatical earlier.
I have 3 more months before I complete a year as an entrepreneur. I'll cover things that have changed for the better by being an entrepreneur after completing 1 year.
For example, I'll cover my balance of long-term planning and execution. I'll cover experiments in work delegation. Hosting cocktail parties. And the never-ending stream of starting pains.
Related posts:
Work delegation: Organizing and Scaling my business as a solopreneur
A sample accomplishment from consulting: Increase Website Visitors By 140%
Consulting learnings: Insights From My Journey And Expert’s Guides
Reasons I might fail: Premortem Of My Career Direction: Lessons From Poker And ‘Thinking In Bets’