Jennifer Schumacher joined the Jukebox Podcast to discuss her 15-year journey in WordPress and web development, and to share lessons from running and working in agencies. Her path began in university with a YouTube crash course on WordPress, moved through freelancing and team collaborations, and grew into running a white-label agency serving other agencies worldwide. Over the years she’s seen successful projects and also toxic cultures, burnout, unbilled work, and broken processes—issues she addressed in a lightning talk at WordCamp Europe 2025.
Why speak at WordCamp? Schumacher explained that many talented people become frustrated by recurring agency problems: people overloaded with support work, projects that deteriorate over time, unpaid work, and staff leaving in frustration. She wants to spark conversations about improving processes and culture so agencies aren’t trapped in “that’s just agency life.” Her talk focused on three concrete, common mistakes and what to learn from them.
The three mistakes
1) Web support that drains your soul
Schumacher described agencies that route all client communication through a single point of contact—usually a project manager. While intended to simplify client interactions, this often creates a communications bottleneck. The single contact rarely resolves technical issues directly; they relay requests to designers or developers who reply with further questions or constraints. Minor changes—like moving a button—can generate hours of back-and-forth, driven less by the work and more by the communication overhead. When agencies absorb those hours instead of billing for them, unbillable time accumulates and becomes unsustainable, particularly for small teams. The result is overworked staff, frustrated clients, and hidden costs that undermine financial health and staff wellbeing.
Lesson: Avoid single-person bottlenecks, make responsibilities and decision rights clear, track support time, and be transparent with clients about what support includes and what will incur extra charges.
2) The design handoff from hell
Another frequent failure is a broken handoff between external designers and developers. Schumacher recounted receiving design files that were inconsistent, lacked clear typographic hierarchy (what’s the H1?), and had mismatched views for different breakpoints. Designs that look great in a mockup can be impractical or inaccessible on the web—issues like contrast, semantics, and responsive behavior often aren’t accounted for. The result: developers spend hours reconciling designs, raising questions, and making judgment calls. If these hours aren’t tracked and billed, teams again eat the cost; if raised late, clients resist additional charges.
Lesson: Define expectations and deliverables before development begins. Use checklists for handoffs (typography, spacing, breakpoints, accessibility requirements, assets, content hierarchy). Foster direct, early collaboration between designers and developers or ensure a clear process for resolving discrepancies. Treat the handoff as a process, not an event.
3) Work more, bill less, and smile anyway
Schumacher described the common cycle where projects start on budget, then scope creep, late requests, browser bugs, and extra polishing accumulate. Budgets tighten, clients expect changes “included,” and teams end up working more for the same pay. When agencies don’t communicate budget limits, scope changes, or invoice for extra work promptly, their effective hourly rate collapses. Many freelancers and small agencies, if they calculated their true effective hourly rate, would find it shockingly low.
Lesson: Communicate budgets and scope transparently from the start and when things change. Track time and flag clients early when requests exceed scope. If mistakes require fixes, absorb reasonable remediation, but for new requests, be explicit about additional costs. Prioritize clarity and early conversations to avoid surprises.
Process, culture, and mental health
Beyond concrete fixes, Schumacher emphasized that processes protect mental health. Repeatedly doing unpaid work and handling chaotic projects leads to stress that bleeds into personal life and relationships. She urged agencies and freelancers to stop normalizing these patterns. Instead, make process improvement a priority: create repeatable systems, set boundaries, and bake transparency into client relationships.
She also stressed that perfect systems don’t exist. Continuous improvement matters: implement pragmatic workflows now, observe, iterate, and adapt—especially as new tools and AI reshape work. Learning from mistakes is more valuable than chasing an unattainable “perfect” setup.
Personal lessons and vulnerability
Schumacher shared a candid personal failure: early in her agency-building days she prioritized team and culture but hadn’t yet learned sales, pricing, or boundary-setting. That led to cash flow problems and ultimately closing the office. She took a sales job to learn how to sell and communicate value, then returned to running her business with improved skills and stability.
Her proudest move is recognizing that the status quo didn’t have to be accepted. She chose to change how she worked—focusing on sustainable processes, less stress, and better outcomes. Her husband’s example of working less and achieving balance influenced her thinking; she stopped glorifying busyness and began prioritizing outcomes and wellbeing.
Practical advice
– Ask peers and mentors: Schumacher highlighted the value of conversations with other agency leaders. Instead of relying solely on viral videos or clickbait “perfect solutions,” ask people how they handle hiring, pricing, sales, and growth. Real stories and practical tips from experienced peers are invaluable.
– Set clear expectations: Use scope documents, checklists for handoffs, and clear support agreements. Make billing rules explicit and discuss them early.
– Track time and cost: Measure effective hourly rates. If numbers are alarming, change processes, pricing, or project selection.
– Be transparent with clients: Communicate when scope or budgets change. Ask for approvals before doing extra work.
– Make process improvement a priority: Small, iterative changes compound. Focus on outcomes, not punching a clock.
Where to find Schumacher
Jennifer is active on LinkedIn and has written a book for freelancers sharing practical advice and stories from her network about cash flow, selling agencies, and systemizing work. She’s planning more community-oriented content (LinkedIn Live) to share conversations and lessons learned.
Closing thought
Schumacher’s message is pragmatic and humane: agencies should stop normalizing chaos and unpaid work, invest in processes that make work predictable and sustainable, and treat mistakes as learning opportunities. By doing so, teams can protect mental health, improve profitability, and build healthier, more resilient businesses.
