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My Unexpected Career Journey & What I've Learned Along the Way

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 What a wild ride these past few years have been! I've bounced from IC to staff engineer to principal and even director-level management where I was setting long-term strategy. Then came the layoff plot twist, which led me to launch two non-tech businesses before circling back to being an IC again—but this time in Operations and DevOps instead of programming. This shift has given me fresh perspective on what actually works and where effort gets wasted.

The contrast between deep-pocketed organizations and bootstrapped startups is striking. One group is carefully carving out their niche while the other is in pure survival mode. What's fascinating (and frustrating) is seeing how much bureaucracy and inefficiency exists, especially for micro-enterprises. These smallest businesses often rely on pen-and-paper systems or basic spreadsheets—stuck with manual processes because there simply aren't tailored tools for their needs. It seems nobody's interested in serving the smallest players in the market.

As a developer, I feel that pull to build something to help these small businesses overcome their challenges. The urge to create solutions is strong, but the reality check is brutal: there's never enough time or engineering resources to improve these situations. From the inside, I now see how these resource constraints force difficult trade-offs. These businesses aren't choosing suboptimal processes because they don't know better—they're making do with whatever's available because they have no alternatives. Without dedicated engineering support or budget for custom solutions, they adapt to limitations rather than overcoming them.

After nearly 25 years in software development, experiencing things from the user/operations side hits differently. I see clear opportunities for impact, but I need to be strategic about what to tackle first. With limited hours and responsibilities that prevent me from going all-in on just one project, prioritization is everything.

More thoughts on this coming soon...

#CareerJourney #SmallBusiness #TechPerspective #DevOps #Entrepreneurship

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