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1 Year From Quitting My Full-Time PM Job. What Do I Miss The Most?

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 consultant.

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5 Things I miss illustrated with meetings, coffee chat, and collaboration. 4 things that  remain the same illustrated with family time and content creation challenges.

What do I miss the most about working full-time?

1 - Regular discussions with a small set 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 kinds of 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 would meet someone virtually, I would remember times we’d met in person. Or imagine 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 - I did not need to pursue every single direction as an employee. Narrowing of 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 taxes tasks. Some had a drag-and-drop interface, for example, expense reimbursement. Some had concierge, like travel booking. The rest did not occupy my mind space, like writing employment contracts or privacy policies.

working collaboratively with colleagues, getting quick feedback, and not needing to handle paperwork

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 give 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 stops 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 when I own my time, I could focus on this. 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.

52 article ideas and 27 article drafts form my content backlog. Content is a big deal but remains a challenge

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.

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