Episode Summary: The Monopoly Report – Episode 53

"A Successful Career in Privacy"

Host: Alan Chapell
Guest: Doug Miller, Privacy Leader and Executive Coach
Date: October 29, 2025

OVERVIEW

This episode of The Monopoly Report dives into the evolving landscape of privacy careers, with a particular focus on building a long-term, fulfilling path in a discipline historically under-structured and frequently misunderstood. Host Alan Chapell interviews Doug Miller – a veteran privacy executive, coach, and former global leader at major digital companies – to explore how privacy professionals can navigate organizational challenges, stay relevant amid regulatory waves, and intentionally reinvent their roles. The episode’s tone is both candid and optimistic, salted with practical advice, personal anecdotes, and encouragement for privacy pros at all stages of their careers.

KEY DISCUSSION POINTS & INSIGHTS

1. The Evolution of the Privacy Profession

[03:00 - 06:40]

• From Accidental to Intentional: Doug recalls that privacy was not a deliberate career path two decades ago; early professionals often "fell into" the field. Today, people are joining privacy intentionally.
• Shift from Reactive to Proactive: The profession has moved from simple compliance and risk assessments ("routinization") to engaging in complex organizational change, including leadership and behavioral influence.
• Impact of GDPR: Doug highlights GDPR as a watershed moment, forcing companies to build mature privacy infrastructures and collaborate across departments rather than siloing privacy to legal teams.
• Data’s Complication: The increasing velocity and complexity of data flows, regulatory sophistication, and the rise of AI are rapidly reshaping privacy concerns.
• Timeless Principles: Despite constant change, foundational concepts like the Fair Information Practice Principles (FIPs) remain relevant.

"I actually would argue that we're going through a turning point where privacy teams and companies are moving from being reactive on privacy issues to seeing the advantages in being proactive... Not everybody's there yet, but I do think that worm is turning a little bit."
– Doug Miller [04:48]

2. Personal Career Journeys in Privacy

[06:40 - 10:08]

• Doug’s Path: Doug’s entry into privacy was rooted in organizational diplomacy and collaborative skills, more than legal expertise.
• The AOL/Time Warner Culture Clash: Using historical mergers as context, Doug and Alan discuss how entrenched corporate cultures can undermine even the most logical strategies.

"The reason they picked me...was because they thought I was diplomatic and collaborative...that was the essence of what the work was going to be...It wasn't just figuring out what the law is going to require."
– Doug Miller [08:06]

3. Building Influence in Organizations

[11:17 - 14:30]

• Overcoming the “Blocker” Perception: Privacy teams struggle when seen as hindrances instead of strategic partners. Success comes from aligning privacy efforts with business goals and shifting conversations from risk avoidance to cost/benefit analyses.
• Making the Case for Investment: Proactive compliance not only reduces risk but streamlines business relationships and future-proofs organizations.

"The trick...is realigning your pitch for the value proposition of the privacy and compliance work to something that the organization actually values, aligning with business strategy..."
– Doug Miller [13:04]

4. The Shifting Regulatory and Enforcement Landscape

[14:30 - 18:29]

• Historical Lax Enforcement: Alan points out that digital media has long benefited from sporadic enforcement, enabling minimal compliance.
• Enforcement is Changing: Doug warns that regulators have grown in expertise and now coordinate efforts, making it “unwise” for companies to assume they’ll go unnoticed.

"I just don't think it's wise for companies to think that they're going to go undiscovered if they're not taking these issues seriously."
– Doug Miller [16:29]

5. Navigating Career Growth and Burnout

[21:33 - 26:04]

• Career Pathways: Doug describes working with privacy professionals at various stages—from aspiring to CPOs—advising that success increasingly demands reinvention, multidisciplinary skills (technical, legal, communications), and “people skills” such as facilitation, storytelling, and alliance-building.
• Mindset Matters: Effective professionals manage ambiguity, persist through setbacks, and focus on influencing organizational culture—echoing F. Scott Fitzgerald's and Ted Lasso's wisdom.
• Burnout in Privacy Roles: Doug references research on types of burnout, emphasizing the importance of forward-facing curiosity and support for colleagues facing similar challenges.

"I am convinced that the profession has changed enough that what got us here won't get us there, that we almost always need to reinvent how we're doing stuff."
– Doug Miller [24:07]

6. Reinvention and Adapting to Change (Especially with AI)

[31:16 - 36:05]

• Facing Technological Shifts as Opportunities: Rather than aging out, privacy pros accumulate “wisdom worker” value by developing leadership and adaptability.
• The ‘And’ in Job Titles: Doug encourages professionals to see requests to take on AI, ethics, or compliance as gifts, not burdens—expanding influence and relevance.
• Continuous Reinvention: The pace of change is accelerating; Doug frames personal career transformation as a journey of discovery, not a threat to identity.

"As we age, we transition into becoming wisdom workers... we are actually more valuable to the organization because of the accumulated wisdom and experience on top of continuing skills."
– Doug Miller [33:16]

7. Addressing Industry-wide Uncertainty and Futility

[38:07 - 41:18]

• Market Pressures: As ad revenue consolidates among tech giants (Google, Meta, Amazon), the sense of futility in the market grows, leading some to “jump to the next sexy thing.”
• Agency Amidst Futility: Doug urges listeners to focus on what they can control: personal growth, embracing new mindsets/skills, and intentionally seeking new opportunities.

"You are never trapped. If you start doing the work on yourself, building your own capacity to change...then you can be more effective in changing the organization."
– Doug Miller [39:42]

8. Takeaways for Building a Fulfilling Career

[43:08 - End]

• Embrace Risk (Especially Early): Alan shares his own story of striking out solo and emphasizes that “every good thing that has happened...came as a result of taking a risk.”
• Reinvention at Any Age: Doug cautions against “job hugging” and advocates for continuous development and preparation for new opportunities—even if circumstances don’t immediately allow for a leap into something new.
• Transferable Skills: Privacy professionals possess diverse skills that translate to a wide array of roles—legal, nonprofit, technical, management—and should honor their journey, not view change as a repudiation of their past.

"There's nothing about reinventing yourself that should dishonor your past. It should be, in fact, respectful of where you've been and grow from there."
– Doug Miller [41:38]

NOTABLE QUOTES & MEMORABLE MOMENTS

• Doug Miller on Organizational Advocacy:
  "If you get out in the organization and you start thinking about what everybody else...is trying to do, it's quite likely that they're feeling some of the same frustration... There's a real opportunity to get out in the organization and start changing, helping everybody else think about how they reinvent their work too." [26:24]

• Alan Chapell on Privacy as Just One Piece:
  "It’s just difficult to talk about privacy without talking about antitrust and without talking about Section 230 and without now talking about copyright law." [22:12]

• Doug Miller on Burnout:
  "We had developed a typology of about 10 different kinds of burnout that privacy pros face because they're not all the same. You can be exhausted, that's not the same as feeling cynical, which is not the same as you're firing on all cylinders but the organization keeps frustrate you." [25:39]

• Alan Chapell on Passion and Career Fulfillment:
  "Find the thing within you that drives you. What is the thing within you that gets you up in the morning? And by the way, I don't want to rule out that that might not be privacy or regulatory." [40:49]

TIMESTAMPS FOR IMPORTANT SEGMENTS

• 03:28 – Doug on the transformation of privacy roles
• 07:20 – Doug’s origins in privacy at AOL
• 10:08 – Culture clash at AOL/Time Warner and lessons learned
• 11:17 – Moving privacy from “blocker” to partner
• 16:29 – Why enforcement is changing and organizations should take notice
• 23:04 – Doug’s framework for coaching privacy professionals
• 26:04 – Addressing burnout and the importance of mindset
• 32:47 – Adapting as a senior privacy pro amid AI and accelerating change
• 39:11 – Overcoming industry futility and embracing agency
• 43:08 – Encouragement to take risks and develop transferable skills

FINAL THOUGHTS & CALL TO ACTION

Both Alan and Doug advocate for self-awareness, risk-taking, and continual reinvention—reminding privacy pros that their skills are in demand both within and beyond privacy. As the regulatory and organizational landscape fluctuates, the truly successful career is one aligned with personal passion, adaptability, and an openness to new opportunities—even if that means forging new paths outside traditional privacy roles.

Doug Miller contact: dougmillerstrategies.com
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