The way we work has changed—and for bookkeepers, it brings both challenge and opportunity. In an episode of The Successful Bookkeeper Podcast, Jennifer Johnston, Vice President of Human Resources at Payworks, reflects on how she adapted her career through key life transitions, and what it takes to thrive in today’s work environment.
Whether you're transitioning from corporate life, launching a solo practice, or rethinking your business after a life event, this conversation offers valuable insights into what really matters when designing a sustainable, meaningful bookkeeping career.
🔄 Embracing Career Transitions
Jennifer’s story is rooted in transition—from working in the corporate sector to building her own business, all while managing life as a parent and remote worker. She highlights how moments of change, even when unexpected, can become launching points for something better.
Key Insight:
Your bookkeeping business can—and should—evolve with your life. Flexibility, clarity of values, and the willingness to adapt are essential.
What to consider:
- Are your current work hours and business model aligned with your personal goals?
- What systems or support would you need to create a more flexible work setup?
🧠 The Mindset Shift: Redefining Success
One powerful takeaway from the episode is how Jennifer redefined what success looked like for her. Instead of chasing growth at all costs, she focused on work that was fulfilling, values-aligned, and sustainable in the long term.
Action step:
Define what success means to you. Is it revenue? Flexibility? Meaningful client relationships? Let this guide your decisions—not someone else’s definition of “success.”
💻 Remote Work Is Here to Stay—Build for It
The pandemic accelerated the shift to remote work, and many bookkeepers have stayed remote ever since. Jennifer highlights how important it is to build strong communication habits, set clear boundaries, and use tools that support efficient virtual collaboration.
Tips for thriving remotely:
- Use scheduling tools and shared calendars to manage expectations with clients
- Create a consistent meeting structure (monthly or quarterly reviews)
- Build processes that support asynchronous communication—clients don’t always need real-time answers
🤝 People First: Clients, Colleagues, and Community
In a world driven by automation, Jennifer reminds us that people still matter most. Great bookkeeping isn't just about numbers—it's about understanding your clients’ needs, supporting your peers, and building community in an increasingly digital space.
Suggestions for connection:
- Schedule regular client check-ins focused on their goals, not just their accounts
- Join peer groups or bookkeeping communities for support and learning
- Celebrate small wins with clients—they help strengthen long-term relationships
The new work landscape isn't about going back to how things were—it's about building something better. Jennifer Johnston’s story is a reminder that clarity, adaptability, and human connection are just as important as technical skills in building a fulfilling, future-ready bookkeeping business.
Whether you're rethinking your business structure, seeking more balance, or adapting to a remote-first world, these moments of change are opportunities—not setbacks.
To hear more about how to navigate transitions and thrive in the evolving world of bookkeeping, listen to The Successful Bookkeeper Podcast.
