Monthly Archives: January 2026
Advice for Mid-to-Late Career Software Engineers

I find myself giving this advice over and over again so I thought it warranted a post.

As an engineer in the mid-to-late stages of your career, you’ve likely accumulated significant technical expertise, but navigating organizational dynamics becomes increasingly crucial for sustained success and fulfillment.

1. Manager Alignment Is the Most Important Thing Governing Your Success in Your Job

In engineering roles, especially at senior levels, your individual contributions—while still vital—are amplified or diminished by how well you sync with your manager’s vision, priorities, and style. Misalignment can lead to stalled projects, overlooked promotions, or even burnout, whereas strong alignment can unlock resources, visibility, and growth opportunities. Think of it as the “force multiplier” for your skills: no matter how brilliant your code or designs, they need managerial buy-in to make an impact.

A personal story: I once accepted a role and a week before my start date I was re-orged under a different manager. I didn’t see any problem at first. I mistook her “hands-off” attitude as trust until she gave away a project I spent a year justifying. Our relationship became adversarial after that. I ended up leaving the company shortly thereafter.

  • Early in your career, success might hinge on raw output (e.g., shipping features quickly). But as you advance, roles involve more influence, mentorship, and strategic decision-making. A misaligned manager might undervalue your architectural insights or block cross-team collaborations, limiting your scope.
  • Companies evolve rapidly—mergers, pivots, or leadership changes can shift priorities overnight. Alignment ensures you’re not caught off-guard and positions you as a key player in those shifts.
  • Data from industry surveys often shows that engineers who report high job satisfaction cite “supportive management” as a top factor, far outweighing salary alone.

How to Achieve and Maintain Alignment:

  • Proactive Communication: Schedule regular 1:1s not just for updates, but to discuss their goals explicitly. Ask questions like, “What are your top three priorities for the quarter?” or “How can my work best support the team’s objectives?” This builds rapport and reveals mismatches early.
  • Adapt Your Style: Observe their preferences—do they favor data-driven arguments, quick prototypes, or high-level overviews? Tailor your deliverables accordingly. For instance, if they’re metrics-obsessed, frame your proposals with ROI estimates.
  • Seek Feedback Loops: Use performance reviews or informal check-ins to gauge alignment. Phrases like, “Am I focusing on the right areas?” can uncover hidden expectations.
  • Build Mutual Value: Don’t just align to their needs; demonstrate how your expertise advances their agenda. If you’re a cloud architect in a company pushing AI, propose integrations that tie into their pet projects.

Signs of Misalignment and What to Do:

  • Red flags include repeated ignored suggestions, lack of resources for your initiatives, or conflicting feedback (e.g., “Innovate more” but no time allocated). If unaddressed, this can erode your motivation.
  • Address it head-on: Politely raise concerns with evidence, like “I’ve noticed our priorities diverging on X—can we realign?” If it persists, consider internal transfers or escalating to HR.

Pitfalls to Avoid:

  • Over-aligning to the point of losing your voice—don’t compromise ethics or best practices just to please.
  • Assuming alignment is static; reassess quarterly, especially post-reorgs.

In essence, treat manager alignment like debugging a system: identify mismatches, iterate, and optimize for peak performance. This can turn a good job into a great one.

2. Your First Loyalty Is to Your Own Career Progression and Personal Happiness

Corporate loyalty is often a myth in modern workplaces—companies prioritize business needs, leading to layoffs, restructurings, or role changes without regard for individual loyalty. By mid-career, you’ve invested years building skills; prioritizing yourself ensures you reap the rewards, avoiding regret from missed opportunities. This isn’t about being self-centered—it’s about balanced reciprocity in an unbalanced system.

Why This Mindset Is Crucial Now:

  • At this stage, you’re likely eyeing leadership roles, work-life balance, or even semi-retirement paths. Companies may not invest in your growth if it doesn’t align with short-term profits, as seen in mass tech layoffs (e.g., 2022-2023 waves at Google, Meta).
  • Personal happiness ties directly to productivity: Burnout from one-sided loyalty can lead to health issues or reduced output. Studies from Gallup show disengaged employees costs companies billions, but the personal toll is yours to bear.
  • Opportunity costs rise with experience—staying in a stagnant role might mean forgoing equity, titles, or networks elsewhere.

Strategies for Prioritizing Yourself:

  • Regular Self-Assessment: Every 6-12 months, evaluate: Am I growing? Is this fulfilling? Use tools like a career journal to track wins, frustrations, and market value (e.g., via salary sites or recruiter outreach).
  • Network Actively: Build relationships outside your company—attend conferences, contribute to open-source, or join professional groups. This creates “escape hatches” for better offers without desperation.
  • Negotiate Ruthlessly but Fairly: When opportunities arise (internal or external), advocate for yourself. If a promotion stalls, counter with data on your contributions. Don’t fear walking away; loyalty doesn’t pay bills.
  • Set Boundaries for Happiness: Prioritize family, hobbies, or health. If a role demands 60-hour weeks indefinitely, weigh if it’s worth it—many engineers pivot to consulting for flexibility.
  • Exit Gracefully: If leaving, give notice professionally, but don’t burn bridges. Frame it as “pursuing new challenges” to maintain networks.

Pitfalls to Avoid:

  • Guilt-tripping yourself—companies don’t hesitate to cut costs; you shouldn’t for advancement.
  • Ignoring warning signs like stalled raises or toxic cultures out of inertia.
  • Over-optimism: Don’t assume “things will improve” without evidence.

Ultimately, this loyalty shift empowers you to craft a career on your terms, leading to greater satisfaction and resilience. Remember, the best companies and managers value self-advocates who bring their A-game because they’re happy and motivated.