In the evolving tech industry, career transitions are becoming more common. This post explores how to navigate these changes successfully, drawing from my experience of three major career pivots aligned with technological shifts.

Key Takeaways:

• Identify emerging tech trends and position yourself ahead of their arrival.
• Leverage your unique skills and experiences to create new opportunities.
• Embrace continuous learning and adaptability.
• Build and maintain genuine relationships to support your career transitions.
• Develop emotional intelligence and leadership skills to complement technical expertise.

After 20 years in Product Leadership, I transitioned to a full-time product leadership coach in March 2024. Throughout my career, I coached product people in my team and externally. I learned I preferred launching people over launching products. That wasn’t my mindset when I started in product management. Over time, the experience I sought changed and ultimately, my career changed as well.

Why Career Transitions Matter in Tech

What’s remarkable about my career change is that it’s my third pivot, each aligning with an emerging technology trend. Growing up in Cupertino shaped my perspective on “emerging” trends, pushing me to identify opportunities before they become mainstream. This approach has been crucial in navigating the ever-changing tech landscape.

I’m sharing this insight because the technology and job scene is changing significantly.

• 86% of employers expect AI and information processing technologies to impact their business by 2030.
• 80% of employers plan to upskill workers with AI training.
• A report by Arize AI found that 281 Fortune 500 companies view AI as a business risk, a 473% year-over-year increase.

Given these statistics, it’s imperative to prepare for an upcoming career transition.

My Journey Through Three Tech Waves

Keep reading to discover how I navigated three major career transitions. This includes my early failures, key breakthroughs, and a framework that emerged from these experiences.

Goal vs Self: The Heart of Career Transitions

Before we dive into the specifics of each pivot, it’s important to understand a crucial concept that guided my journey: the balance between Goal and Self, which is a riff on Goal vs Soul.

In career transitions, we often focus on goals – climbing the corporate ladder, hitting performance metrics, or mastering the latest tech stack. These are important, but they’re not the whole picture. Equally crucial is nurturing our sense of self – finding work that aligns with our passions, contributes meaningfully, and allows for personal growth.

• “Goal” represents the external career objectives and measurable achievements others have assigned to us (parents, society, etc.)
• “Self” represents our own personal skills, interests, values, and working style that inform our career choices

As you read about my transitions, notice how each move wasn’t just about reaching a new professional goal, but also about aligning my work more closely with what resonated with me, my sense of self. This balance is key to a truly successful and satisfying career journey.

Pivot 1: The Lean Product Development Shift

I graduated with a communications degree, applicable to anything or nothing. I chose it because I was fascinated by how people interact with technology. I tried programming, but my brain didn’t work that way. I identified many ways to proceed and was more curious about people than machines.

• DS Lesson – If you enjoy something and the direct path isn’t viable, find an alternative that keeps you connected and involved.

Like today, the market was terrible. I had internships throughout university and discovered I liked interviewing people and writing about new developments. I sat down with my manager to brainstorm my degree and experience options. All ideas were worth considering. We discussed my favorite classes (business, strategy) and those I dreaded (math, anything with standardized tests). Included was a future goal of going to business school. We agreed to apply now and see what happened. No harm in trying.

• DS Lesson – You’re not alone. Connect with others who’ve done it. Their real experiences will shape your next step.

Filling out applications was a trudge, but I was used to it. I grew up playing sports. To compensate for not having natural talent, I worked harder than anyone else. I put in the hours, practiced, and always showed up. This grit and tenacity became my superpower.

• DS Lesson – If you want a goal badly enough, be prepared to do the challenging work to get there.

After grad school, I had a hard time finding a job, even with an MBA. The market was still bad. My breakthrough moment came when I discovered I was good at working with stakeholders – those communication skills came in handy. Through connections, I joined my first startup. It wasn’t the exact role I wanted, but I got in the door.

• DS Lesson – Reflect on your life and identify what you enjoyed. Was it easy or hard? What has the experience taught you about yourself?

Networking remained vital in my career. I applied curiosity and enjoyed getting people to talk about themselves. I earned a degree in human-computer interaction and became a User Experience Researcher at Salesforce, which led to my first Product Management role – my dream job.

• DS Lesson – Some folks value certificates and get them for everything, while others don’t. Do what feels natural and aligned to you and the role you seek.

Monster UK/IE sought a product manager with a user experience background for a startup environment. I oversaw a team of three – 1 product manager, 1 data analyst, and 1 content designer, soon joined by another PM. My boss was amazing. I had a great group of friends at the company and continued to do well.

We applied lean product development principles to improve the job search and CV (resume) creation process, enabling Monster to lead in the UK and Ireland. After this success, we continued to apply customer feedback and rapidly iterate to introduce Monster’s first eCommerce platform in Europe. This resulted in my role’s growth to lead all of Western Europe (9 countries) and a team of 15.

A startup contacted me to head up their product team of two. I was honored and excited, so I took the plunge. Within months, things went wrong. Even though I applied my learnings from Monster, my peer in Program Management started attacking me. I recommended moving away from requiring 100+ pages of functional requirements documentation, which prevented any learnings or changes. They were stuck in the past and hadn’t caught on that lean product development was the way forward.

• DS Lesson – Know when to walk away from your dream. It will still be there. Acknowledge that the timing or conditions may not have been right.

I had never faced such frequent and intense verbal attacks. I talked to my boss and the person who hired me. They were shocked but didn’t know what to do and did nothing. I left. Ironically, the company lasted another year and was bought by a competitor.

• DS Lesson: What key tactics helped me through career pivot #1?

Look for upcoming industry shifts and get ahead. If you can’t land your dream job immediately, start with an adjacent opportunity. Build and maintain genuine relationships to jump the queue ahead of other job seekers.

I had tenacity on my side. I made my background work by staying flexible about my career entry point while focusing on my next dream job.

Time for career pivot #2.

Pivot 2: Mobile-first and app-based ecosystems

I decided to explore more roles on my bucket list. Working for a digital agency would let me experiment with emerging technologies. I contacted Razorfish, a top digital media agency. I emailed, phoned, and shared my work until the head of strategy agreed to give me 30 minutes. I prepared by talking to agency people, researching, and learning about their clients. My knowledge of emerging trends, including lean product development, got me a role on the strategy team.

• DS Lesson – Trust your judgment. My early product insights created opportunities elsewhere. Those instincts matter.

I was a sponge. Curiosity and a desire to learn were my friends. I knew emerging media trends inside and out. I guided clients and the agency to prepare for what’s next, leading me to start the Emerging Media group in London covering app development across mobile, social, and digital out of home. Despite the experience, I missed building and seeing them develop. Clients took on that role.

I returned to product management with a twist, combining innovation and emerging media, experiences that others didn’t have to the same level. Leveraging these skills helped me to create the Future Technologies team at Pearson.

• DS Lesson – Channel your passions into your work. Genuine enthusiasm sets you apart from those just checking boxes.

At Pearson, I leveraged my Razorfish and social media experience to build a digital-first community of “influencers” called the Future Technologies Champions. The mission was to foster innovation, accelerate digital transformation, and identify emerging trends impacting Pearson’s business. Starting with five individuals recommended by my manager, I grew the community to 150 members across global business units in three months through outreach and networking.

Champions were selected for their passion for emerging technologies, including mobile and social. They contributed by voting on quarterly topics, generating measurable outcomes like cost and time savings by sharing insights with their teams. We launched Pearson’s first augmented reality mobile application and initiated a digital credentialing platform, which merged with Credly and later bought back by Pearson.

Participation became a professional achievement, with members showcasing it on LinkedIn and resumes, cementing the community’s role as a driver of innovation and growth.

• DS Lesson – Impact culture by building bridges. Leverage networking skills to find allies across teams and shape your environment, regardless of your level.

A new CEO joined Pearson, and times changed. My network enabled my transition to another part of the business where I continued to move up the product leadership ladder. Multiple teams merged into the group I oversaw, expanding my purview. Relying on my curiosity about what makes people tick, I identified ways to unite the diverse bunch. I didn’t do it alone. Brainstorming and valuing all ideas played a role.

My next career pivot began to emerge. I loved Product Management but enjoyed coaching my team even more. A team member struggled with public speaking. I encouraged them to find a local meet-up and present about our project. They did it because they knew I had their back. Now they led workshops worldwide.

• DS Lesson – Use your growth lessons to help others. I encouraged people to step out of their comfort zone and take chances to develop their careers.

COVID hit and everything was changing (again). It was time to move on. I led the Product and Design team at SimplePractice and a Product team at the Chan Zuckerberg Initiative, but the coaching voice in my head grew louder.

AI was taking off. If machines are to replace humans (again), what makes us human will be the differentiator. Bernard Marr, futurist, board advisor, and author of “Generative AI in Practice,” identified the following critical skills for 2025 in his recent Forbes article.

1. AI Fluency: The New Digital Literacy
2. Digital Transformation Leadership
3. Perpetual Learning Agility
4. Strategic Foresight and Complex Problem-Solving
5. Emotional Intelligence: The Human Edge

I can help others with 2 through 5 through coaching and 1 via my experience.

I went into introspective mode. I reviewed my career feedback. The common themes are that people see me as a resilient leader who embraces challenges with a product-driven mindset. I create a space for others to grow, learn, and achieve clarity. I make people feel both seen and capable.

Time to acknowledge what others saw and embrace my next career change.

Pivot 3: AI Revolution

Starting my own business wasn’t easy. I know people who left startups and got coaching gigs through prior employers and VCs. I didn’t start a company and lacked VC introductions. I didn’t go to an Ivy League and hadn’t worked at a MAANG. What I had was grit and tenacity. I was the product I had to develop. I was the product of my prior efforts.

• DS Lesson – Own your wins and losses, big and small. Reflect on what made them happen so you can create more successes ahead.

I found adjacent opportunities and a path to increase my knowledge. I took coaching courses, wrote a book titled Next-Gen Product Management with two other product people (released Jan 7th), continued learning about AI, and leveraged my network to obtain my first coaching clients.

To build my brand, I focused on my blog and fine-tuned my style. Feedback led me to the tagline People-First Product Leadership, which evolved into People-First Leadership as friends highlighted the principles applied to leaders outside Product.

Networking remains critical. I contribute to two companies integrating AI, coaching, and product management – SelfActualize and Wizly – and other startups, including Gildre and Inciteful. For example, my experiences power an AI-twin for Wizly, a digital representation of an expert’s knowledge, designed to interact with users and provide insights 24/7.

This integration of my coaching expertise with AI technology demonstrates how human skills and AI can work together to enhance professional development. As AI handles more analytical tasks, leadership will place greater emphasis on emotional intelligence and the ability to motivate and inspire teams – which is my coaching sweet spot.

• DS Lesson – Career transitions are rarely straightforward.Stay curious and apply learned strategies to navigate your career change confidently.

Navigating Career Transitions

Based on my lessons highlighted above, the following patterns emerge. They can assist others in determining their next move, planned or unplanned.

Career Pivot Playbook

Phase	Key Actions	Focus Areas
Recognition Phase	Use LinkedIn, newsletters, and expert insights to observe industry trends.	Awareness of emerging technologies and market shifts
	Reflect on alignment between trends and your strengths, values, and interests.	Understanding how your skills fit in the evolving landscape
	Seek insights through exploratory conversations with peers, mentors, and leaders.	Identifying potential opportunities
Preparation Phase	Identify skill gaps and pursue targeted learning through courses and workshops.	Closing expertise gaps and building confidence
	Reconnect with past colleagues and expand your professional network.	Establishing meaningful and intentional relationships
	Share thought leadership via blog posts, LinkedIn, or webinars to build credibility.	Positioning yourself as a relevant voice in your target field
Transition Phase	Outline a clear pivot strategy, including target roles, companies, and timeline.	Developing a structured and realistic approach to the pivot
	Update your resume and LinkedIn to showcase transferable skills and measurable achievements.	Demonstrating relevance and adaptability
	Apply for roles, leverage your network for referrals, and practice interviews.	Gaining job market traction through tailored efforts
Growth Phase	Spend the first 30-90 days integrating into the company culture and identifying quick wins.	Building credibility and establishing yourself in the new environment
	Continue skill development, seek feedback, and cultivate mentorship.	Accelerating learning and refining expertise
	Share contributions internally and externally to align personal and company goals.	Building long-term value and brand visibility

Common Mistakes to Avoid During Career Transitions

There are patterns of behavior that can help or hinder career pivots, which I learned through my transitions and coaching others. Mistakes are part of any journey, and being aware of common pitfalls can help navigate changes smoothly. Here are key mistakes to watch out for, along with approaches that have worked better for me and my clients.

1. Feeling Trapped by Familiar Patterns

During transitions, we often revert to familiar patterns. These habits can be helpful or hurtful. For example, you might react defensively to a slow job search or fixate on every rejection.

• Mistake: Letting old negative habits guide your response.
• Better Approach: Notice patterns. What physical sensations, emotions, or stories arise? Reframe negative thoughts. Add “not yet” to embrace possibility.

2. Letting Fear of Starting Over Paralyze You

Starting over is terrifying. I learned progress comes from small steps.

• Mistake: Waiting until you feel prepared.
• Better Approach: Lean into what you enjoy, for example writing articles or working on your brand. Each small action adds momentum, reminding you that progress isn’t always straightforward but is achievable.

3. Minimizing Your Achievements

My husband pointed out that I downplay achievements, like obtaining a new role or helping a client get a promotion.

• Mistake: Rushing past wins without acknowledging them.
• Better Approach: Acknowledge your wins. Celebrating success reminds you of your progress and impact.

4. Mistaking Resilience for Constant Work

I’ve always been a hard worker. Over time, people called me resilient. Resilience is powerful, but it’s tiring as it feels like you’re constantly working to prove yourself.

• Mistake: Pushing yourself without rest.
• Better Approach: Allow yourself to breathe, even just for a few minutes. Hard work is necessary, but observing the ride matters too. Show up in a way that is sustainable and authentic.

5. Overlooking Continuous Learning

In rapidly evolving tech fields, what’s cutting-edge today may be obsolete tomorrow.

• Mistake: Assuming your current knowledge suffices for future roles.
• Better Approach: Dedicate time weekly to learn about emerging technologies and trends in your field. This involves reading blogs like this one, taking online courses, or attending tech meetups and conferences.

Conclusion

Navigating career transitions in the ever-evolving tech landscape requires adaptability, continuous learning, and a people-first approach. Each transition is an opportunity for growth as shown through my journey from lean product development to mobile-first ecosystems and now the AI revolution.

As you consider your career pivots, remember:

• Stay ahead of emerging trends
• Leverage your unique experiences and skills
• Embrace change and continuous learning
• Build meaningful relationships
• Develop technical and emotional intelligence

The tech world offers possibilities for those willing to leap and learn along the way. You can ride the waves of technological change and build a fulfilling, dynamic career in tech by following these principles and avoiding pitfalls.