Reflections on My MacAdmin Journey
A reflection on my life and career journey as I perform a Career Audit.
This year, I’ve been reflecting on my life and career journey; where I’ve been where I’m headed next. As a result, as well as being inspired by conversations with friends, colleagues, and countless LinkedIn posts, I decided to perform a career audit—my way of checking in with myself and mapping out future ambitions.
Before diving into this reflection, I followed a structured framework—a set of deep-dive questions I’ve compiled from various online sources to guide my career audit and have something re-usable to be able to regularly update my own auditing. I looked at every job I’ve held, asked myself what worked and what didn’t, where I thrived, what I struggled with, and how I’ve grown.
If you’re interested in performing a career audit of your own, I’ve made my personal template available on GitHub. It’s the same one I used to write this post—adapted for tech professionals who want to reflect with depth and clarity.
From Retail to Enterprise
My career began modestly—stocking shelves at a local grocery store, selling computers and tablets at Best Buy, and later providing tech support at Apple. These roles taught me more than just technical troubleshooting; they gave me valuable skills in patience, empathy, and effective communication. I vividly remember helping customers recover lost photos, or explaining to elderly customers that due to not “believing in the cloud” that their years of memories is gone forever, and navigating intense Black Friday shifts before Black Friday turned into a mostly online experience.
Best Buy Reflections
I was happiest at Best Buy when one of my best friends Andre and I had the same shifts. He eventually moved on to TV sales, but those shared hours on the floor made work something to look forward to. And then there was Chet—the Apple Guy. He was an Apple Rep assigned to our store and ultimately the one who pushed me to apply to AppleCare when I started to feel it was time to move on. That encouragement—his and others later in my career—genuinely shaped my journey.
There weren’t many unhappy moments at Best Buy, but one I’ll never forget: working the night before Thanksgiving to prep for Black Friday, then being back in the store for the big rush—only to fall asleep standing up during my shift. Horrible… but memorable.
Apple At-Home-Advisor and Retail
I moved from being an At-Home Advisor with AppleCare to a Technical Specialist within Apple Retail. That shift brought out the best in my soft skills. I was happiest when I could help customers realize the problems they didn’t even know they had—usually tied to their lack of understanding around the tech they used every day.
I made some lifelong friends during my time at Apple Retail, especially at the Shadyside, PA store. For a while, it truly felt like a “family” environment—even if I don’t necessarily believe in that phrase anymore in a workplace context.
But not everything was rosy. My time at the Shadyside location ended on a sour note. I was a Technical Specialist, focused on helping people—not on sales. When store leadership rotated and I got a new manager, things changed. Suddenly, I was being judged on my accessory sales, even though I routinely passed those off to sales associates. I couldn’t reconcile that shift in expectations. I transferred out rather than compromise what I felt was integrity in customer service.
Before that rotation, I felt like I was thriving—thanks to my manager, Dan. Dan mentored me in all things customer service and understood that sales didn’t have to come at the expense of doing what was right. Dan, if you’re reading this—thank you. You truly left a lasting impact.
While I didn’t have a formal resume bullet for this role, I always thought of my time at Apple as solving ‘human problems’ with tech—helping people navigate digital grief, confusion, and sometimes even their first iPhone. That might not show up on a KPI dashboard, but it shaped how I approach user empathy to this day.
Apple’s credo at the time—Enriching Lives—hit me hard and still resonates:
“We are here to enrich lives. To help dreamers become doers… to do the best work of our lives… At our core, we believe our soul is our people.”
That value set, even if not always consistently lived out in practice, helped shape how I see leadership and purpose today. I still have the credo saved to my Apple Wallet nearly ten years later.
The Leap to Enterprise IT
Transitioning to Carnegie Mellon University’s (CMU) Software Engineering Institute (SEI) was my first true step into enterprise IT. It also happened to be my first taste of working in the federal space as the SEI is a Federally Funded Research and Development Center (FFRDC) working under the U.S. Department of Defense (DoD). I had no prior enterprise experience, but my knowledge of Apple products, strong soft skills, and willingness to learn helped me land the role.
I was thrown right into the wonderful world of Mac management, and Jamf Pro, and used my early days to be a sponge, soaking in as much knowledge as my brain allowed. I would say I was happiest when I transitioned from User Services Consultant to Senior User Services Consultant. My work building and expanding the Mac@SEI platform was recognized widely—from help desk colleagues to the CTO and CEO. I had a manager who listened when I vented about wanting to move up, and though advancement was limited, they fought for me while i continually fought for myself. While I was unable to have a dedicated Mac Systems Administrator role created for me to fill and moving to the Windows Engineering team, becoming Senior User Services Consultant on the Help Desk / User Services team was a welcomed compromise.
Even during the COVID-19 pandemic—while juggling transition plans, remote work prep, and expecting a third child—I still found purpose in the chaos. Those days weren’t happy ones, but the unhappiness wasn’t caused by work. It was the world turning upside down.
My whole time at SEI felt like a stretch of thriving. I was given freedom to build automations, mentor others, and develop internal processes that boosted our help desk’s performance. I even lightened the mood by regularly setting my Teams status to something comedic which would make its way around the office chats.
I was filling the role of a dedicated Mac Admin even before one formally existed at SEI. My work spanned everything from Tier I to Tier III support, implementing Jamf App Installers, and even writing the KBs others would use to triage their own issues. I took pride in making the entire help desk smarter, not just in fixing individual tickets.
The culture at SEI valued growth, trust, and autonomy. My leadership—from manager to CTO—invested in me. I was seen and supported, and that confidence carried into every project I took on. While I left for growth and better career opportunity, the relationships I’ve built within the organization are invaluable to state the least.
Expanding My Scope
Joining Compucom meant scaling up in a big way. As part of a managed service provider, I was embedded within client organizations, which felt… odd at times. I had more day-to-day interaction with clients than my own company.
Still, I was happiest swapping “battle stories” with another Mac admin friend on my team—one I still keep in touch with. Those shared experiences kept me grounded and broke the sense of isolation.
I thrived here because I was trusted. My manager gave me full autonomy to make the right decisions for my client. No micromanagement, just support when I needed it. My work spoke for itself, and I never had to chase credit.
I acted as a full platform engineer—keeping the Mac@Work Platform modern and well-prepared for the fast-paced changes of macOS. I didn’t just keep the lights on. I preemptively tested macOS versions, implemented the CIS Benchmark via mSCP, and even reconciled discrepancies between mSCP audit results and Qualys scans. Anyone who’s ever had to deal with a Qualys scan not matching what mSCP, or CIS’s official documentation – if you know, you know. I also regularly communicated updates to stakeholders, helping them stay ahead of changes before they became blockers.
Due to Compucom being a registered Partner with Jamf, I had access to additional resources, documentation, learning, and tools to enhance my knowledge and best practices to deliver exceptional service to the client. This allowed me to obtain partner specific certifications, like the Jamf Management Consultant, Engineer, and Integrator certifications. These Partner-specific certifications have helped me stand out and above some of the competition when I had begun my job search again. But beyond that, I helped to mentor the help desk in tier two level troubleshooting, which selfishly helped myself as the end result was less tickets being escalated to me.
Jamf Certified Integrators are able to use their deep knowledge of Jamf’s products to deliver top-tier services and support for Jamf Customers. The Jamf Certified Integrator can present Jamf solutions, deliver Jamf services, troubleshoot issues and provide support for the most complex customer needs.
Federal IT and Leadership
Returning to federal IT via Indigo IT, and now Akima (Cloud Lake Technology), I’ve taken on some of the most complex challenges of my career at U.S. Customs and Border Protection (CBP) under the U.S Department of Homeland Security (DHS). I’m currently serving as a Senior Operations Engineer and Team Lead for the Mac Platform.
I’ve introduced and enhanced modern best practices to the platform—such as using the macOS Security Compliance Project not just to enforce the DISA STIG baseline but to provide organized, well-documented reporting.
I’ve worked hard to move the engineering team from a reactive posture to a proactive, solutions-oriented mindset. That includes creating a growing knowledge base, mentoring junior engineers, and involving them in “big picture” projects so they feel empowered to contribute at a strategic level. And all of this, I believe, has freed up our Apple Engineering Architect to fulfill their prime role as a people manager for the Mac Engineering group. Our Apple Architect has maintained the group, and I have been able to come into my role a their right hand to do the implementation and the project work that had not been able to get off the ground – all the while feeding the rest of the team as much knowledge as possible.
Working alongside one Junior Engineer who serves as a dedicated Mac Application Patch Engineer, we’ve also optimized patch workflows—reducing vulnerabilities, increasing compliance, and speeding up adoption rates across the board. Another Junior Engineer has taken up a specialization in endpoint security, sharing their knowledge and assistance with implementing mSCP in the best possible way for the org. And there are more examples of the Mac Support engineers filling in more specialized responsibilities or having their own knowledge where they’ve been the team expert for.
That mentorship has paid off—as I feel that junior engineers are more self-sufficient, confident, and proactive. They’ve started making platform improvement suggestions without prompting. We’re no longer bottlenecked by senior guidance for the most part.
CBP’s historically Windows-centric environment initially led to siloed workflows between our teams. But that’s changing. We’ve built strong collaboration between Mac, Windows, cybersecurity, and networking teams, which has made our policies more consistent and the user experience better for dual-platform users.
This work has helped modernize CBP’s macOS environment, enhance compliance, and build a stronger, more capable engineering culture—all while directly supporting the agency’s mission success.
Growth, Maturity, and Confidence
Over time, I’ve come to appreciate how small, steady progress adds up in huge ways. You don’t always notice you’re leveling up until you stop and reflect—or lead a team of junior engineers and realize just how far you’ve come. I’ve built up a decade of experience managing macOS daily, and it shows in how I troubleshoot, how I mentor, and how I build scalable, secure platforms.
Spending time in the Mac Admins Slack helping others has also revealed something to me: I know my stuff. It’s taken a long time to say that confidently (and maybe a little awkwardly), but I’ve earned that confidence.
Lessons Learned
Throughout my career, I’ve discovered several core truths:
- Mastering basic skills—troubleshooting, scripting, networking—is fundamental.
- Documentation, documentation, documentation. It’s far easier to have someone follow an 8-step guide than to repeat the same process verbally every few months.
- Automation isn’t optional; it’s essential for effectiveness.
- Understanding “why” something works is just as important as knowing how.
- The community—especially the MacAdmins community—is invaluable for professional growth.
I’ve also learned that aligning with an organization’s culture and values greatly impacts job satisfaction. Apple’s credo about enriching lives still resonates with me deeply, and supportive leadership experiences at SEI left lasting impressions.
Looking Ahead
Looking towards the future, I believe my next goal is to step into an Individual Contributor (IC) role like Client Platform Engineering role, blending my skills in macOS Management, Security automation, and Endpoint Security.
I’ve had a taste of performing as a CPE in various roles throughout my career and it’s the ideal next step. It allows me to move upwards without going into a managerial track. Becoming a manager isn’t the only option that exists when considering how high one will go within their IT career.
“Client Platform Engineering teams deploy, manage, secure and decommission endpoints at an enterprise scale. The main goal of the team is to provide an excellent user experience to every employee and set secure defaults from day one…” — Kane Narraway, What is Client Platform Engineering
But I’m also considering a parallel path—macOS Security Architect or Zero Trust Endpoint Engineer—roles that lean heavily into my security expertise and still aren’t ones that immediately require me to move into a people manager role. But managerial roles are one I will take if life leads down that path. The enterprise world is demanding more than MDM administration today. With the rise of Zero Trust, regulatory compliance, and security automation, organizations need engineers who can turn frameworks like DISA STIG and NIST 800-53 into scalable, automated enforcement models.
That’s already what I’ve been doing: integrating mSCP, auditing fleets, and customizing Jamf Pro and other security-related tools to align with ever-tightening security requirements. I’ve shown I can lead security transformations in regulated environments like CBP, and I’ve built a foundation that aligns perfectly with those higher-level security architect roles.
Chris Lo calls out on LinkedIn that many organizations stand up Apple-centric infrastructure and ecosystems, and then begin hiring as they do for their Windows platform - not accounting for the nuances of Mac Management.
Companies move to Apple infrastructure - They roll out Jamf, Kandji, Intune, ABM - And then they try to hire the way they always have. That’s where it goes wrong. Because hiring for Apple IT roles requires a completely different lens. – Chris Lo [LinkedIn]
So whether I take the route of Client Platform Engineering, or pivot fully into a macOS Security Architect role, I know where I add value: building secure, scalable, user-centered Apple environments.
To get there, I plan to:
- Pursue advanced security certifications like CISSP (Certified Information Systems Security Professional) or CISM (Certified Information Security Manager).
- Continue sharing insights through writing, mentoring, and open-source contributions.
- Deepen my experience with threat modeling, EDR integration, and Zero Trust frameworks for macOS.
No matter the direction, the common theme remains the same: bridging macOS, security, and automation at scale.
That next phase won’t just be about technical growth—it’ll be about influence and impact. I want to be a name on published benchmarks, contribute to open-source tooling, and ensure macOS security isn’t an afterthought in any enterprise setting.
My Career Roadmap: From Now to Next
Having a vision is important—but turning that vision into action takes structure. Alongside this audit, I built out a detailed career roadmap** to help guide my next few years. Whether I stay on the path toward Client Platform Engineering, pivot deeper into macOS Security Consulting, or grow into a Staff or Principal Platform Engineer role, this plan helps me stay intentional.
I do believe it’s important to point out that with the current job market and my understanding of growth opportunities within my own organization, this roadmap may not occur in the method, time, or order detailed below. But the goal is to have something that I can say that I am working daily to achieve, where ever that may lead me.
Here’s how I’m mapping things out:
Phase 1: Strengthen Leadership & Strategic Influence (0–12 months)
Objective: Elevate my leadership profile and deepen impact on security, automation, and Apple platform engineering.
- Expand cross-functional collaboration with security, networking, and compliance teams.
- Formalize mentorship programs for junior engineers and help desk staff, or continue through the Mac Admins Foundation Mentorship program.
- Automate Jamf Pro security enforcement—targeting a 80+% reduction in manual checks.
- Contribute to the macOS Security Compliance Project (mSCP) v2 development and other open-source tooling.
- Share internal documentation with leadership; publish external technical blogs.
Phase 2: Position for Senior IC or Architect Roles (12–24 months)
Objective: Transition into a Client Platform Engineer, macOS Security Consultant, or Staff/Principal Platform Engineer role.
- Complete non-Mac focused, advanced certifications: CISSP, CISM.
- Design an enterprise-wide Apple security roadmap aligned with Zero Trust and industry frameworks (NIST, DISA STIG, and others).
- Lead internal working groups or advisory boards around Apple device strategy.
- Speak at industry conferences and webinars such as (MacAdmins Podcast, Jamf Nation User Conference - JNUC, and Penn State’s MacAdmins Conference.
Phase 3: Establish Deep Domain Expertise (24–48 months)
Objective: Build recognized expertise across macOS security, endpoint engineering, and automation at scale.
- Grow into a recognized security or platform architect leading Apple strategy across teams.
- If consulting: establish a macOS security automation business or training program.
- Collaborate with Apple, Jamf, or other vendors on platform compliance and tooling evolution.
- Contribute to open-source security tools, STIG frameworks, and mSCP extensions.
Beyond 5 Years: Executive Influence & Thought Leadership
Objective: Grow into a Director of Apple Platform Engineering, CTO, or Chief Security Architect or Information Security Systems Officer (ISSO) roles in Apple-centric enterprise environments.
- Drive Zero Trust strategy and compliance for Apple platforms at scale.
- Manage a team of 15+ engineers or consult across multiple federal/commercial clients.
- Influence vendor roadmaps and industry security standards (Jamf, Microsoft, CIS).
- Publish a book or curriculum on scalable macOS security.
You can view or reuse my roadmap template on GitHub.
Personal and Financial Stability
I’ve progressed from minimum-wage jobs to a somewhat comfortable six-figure salary, successfully negotiating better compensation along the way. At one point, I secured a new role with over a 50% salary increase—because I knew the importance of having to advocate for myself, especially as a Black man in America. I used to be just happy to get any bump in pay, but after successfully negotiating my salary at Indigo IT and landing the top of the posted range, I realized I had more power than I thought.
From earning $8/hr at Best Buy to now surpassing the industry average for macOS engineers, the financial growth is undeniable. According to Dice’s 2025 Tech Salary Report, professionals with macOS skills earn an average of $115,371. I’ve crossed that threshold—but even then, it doesn’t always feel “comfortable” in today’s economy. Inflation eats away at progress, and while I can weather a $1,000 emergency, I’d feel more secure being able to absorb a major curveball—like a layoff or unexpected family need—without fear. You can read more about Dice’s 2025 Salary report here.
A big turning point came early in my career actually, when my wife and I realized her entire paycheck would go toward childcare if she stayed working after our first child was born. So she became a stay-at-home parent. Then came a second child, the pandemic, a third child, and a remote job that allowed me to be the go-to parent for school pickups and drop-offs. That freedom has become essential—not just to my day-to-day sanity, but to our family’s financial sustainability. I have tried to maintain a firm “remote-only” requirement now, not just for convenience, but because it’s baked into our life strategy. It saves us from paying for before- and after-school care and gives our family back precious time and the ability to invest back into ourselves. My wife is going back to school to obtain her masters after recently re-entering the workforce fulltime.
While I’ve done well financially from a salary perspective, I’m deeply aware of how fleeting things can be. A sudden job loss would be a serious blow. My long-term goal is clear: financial independence, so my family and I don’t have to worry about whether the bills will be paid if something unexpected happens. I don’t need a mansion or to travel the world. I just want stability, peace of mind, and the freedom to enjoy the life we’re building—without working myself into the ground. And I know how challenging it will continue to be to obtain financial freedom with the current economic events facing both the United States and the World in 2025.
Defining My Legacy
Ultimately, I want to be known as the person who makes macOS security and compliance seamless at scale. Not the guy who just applies CIS benchmarks or some other baseline, but the one who helps others automates them, enforces them intelligently, and ensures they don’t break user workflows.
I want to be recognized for helping in the mentoring of the next generation of Mac Admins and engineers. There aren’t enough professionals who understand both Apple IT and security at a deep level—and I want to help change that.
In short, I want to be the go-to expert for building secure, scalable, and automated macOS environments—whether that’s in federal agencies, Fortune 500 companies, or through open-source contributions that push the industry forward.
Before retirement, my north star is financial independence. I want to reach a point where my family doesn’t worry about what comes next. No more paycheck-to-paycheck anxiety. Just enough stability to live fully and freely.
That’s why I give back through mentorship with the Mac Admins Foundation, where they’ve ran a pilot program supporting professionals at all levels of their careers as they navigate the challenges of Apple IT. It’s incredibly rewarding to see someone gain confidence, build expertise, and find their place in this field—especially knowing I played a small role in that growth. And on the flip side, my mentee spoke right back into my career as we were at rather equivalent positions in our respective organizations, making it less of a mentor-mentee relationship but two people feeding into each other’s life and work.
I also volunteer my time in the Mac Admins Slack community, answering questions, sharing scripts, and troubleshooting weird edge cases. It’s more than just helping people—it’s about strengthening the entire ecosystem. The Slack community helped me immensely earlier in my career, and now I’m proud to contribute to the same space that shaped me.
Community isn’t a side project—it’s part of my identity as an engineer and a leader. Just as others poured into me, I’m committed to paying that forward.
In short, I want to be the go-to expert for building secure, scalable, and automated macOS environments—whether that’s in federal agencies, Fortune 500 companies, or through open-source contributions that push the industry forward.
Before retirement, my north star is financial independence. I want to reach a point where my family doesn’t worry about what comes next. No more paycheck-to-paycheck anxiety. Just enough stability to live fully and freely.
Final Reflections
Looking back, I’m grateful for every step—from retail counters to federal agencies. Each experience taught me valuable lessons and prepared me for the next challenge.
In every role, I’ve found myself solving problems that technically may not have been mine—because I couldn’t ignore the opportunity to make things better. That’s not something you put on a resume, but it’s central to who I am as an engineer and a teammate.
As I move forward, I remain committed to continuous growth, community involvement, and leaving a meaningful impact in the macOS and IT engineering communities.
Responsible GenAI Use
This blog post reflects my lived experience and personal growth—but to shape and refine it, I used a few trusted AI tools:
- ChatGPT – for organizing and clarifying thoughts
- Notion AI – for editing and structural drafts
- Apple Intelligence – for summarization and reminders
- Grammarly – for grammar correction, suggestions, and proofreading
These tools acted like co-pilots—helping me connect the dots, polish my language, and turn scattered notes into a narrative I’m proud of.
I believe in responsible use of generative AI—transparent, ethical, and human-led. If you’re exploring similar reflections or want to level up your documentation and storytelling, I encourage experimenting with GenAI as a productivity aid—but always with authenticity and transparency at the core.