Unbeaten Path: A Career Journey

A different Trajectory

My career in digital strategy and content management did not go through the typical route via a web or design agency. Over the years, I’ve been a subcontractor for several agencies, hired and collaborated closely with agencies, and created in-house digital operations at several employers. However, I didn’t cut my teeth in an entry-level agency job nor learn one specific skillset through formal training stage by stage, which is the industry norm. I took a different path by choice and by happenstance. 

The unusual journey doesn’t fit the standard employment niche in the digital profession, but it has provided me with a broad perspective. For those of us who came up outside of the agency system, we built an eclectic professional toolkit from which to draw.  

Origin Story

Many English Literature majors of my generation were forced to be inventive and create a career for ourselves. In the academic degree mills that pumped out lawyers, doctors, and engineers, choosing a liberal arts degree was an act of defiance and self-determination. Pursuing graduate/doctoral studies was a dead end, as our professors warned and their career struggles exhibited. Before the digital profession existed, we didn’t have jobs waiting for us upon graduation. Thus, we learned to be broadly curious, resourceful, and adaptable. 

As luck would have it, the digital medium was burgeoning and needed “editors” in as-yet undefined roles. Marketing, web design, and IT agencies hired eager young graduates and trained them in the agency model. A few of us forged ahead on our own. 

Early Career Steps

My first position was in a large public university. A couple years in, someone in the IT department tapped my shoulder because they needed a “world wide web editor” to support online administrative/transactional sites under development. I jumped at the opportunity. I learned HTML, design, web writing, and user experience—and the capriciousness of the digital content field. When the websites launched, I was out of a job. My tasks were spread amongst various communications and secretarial staff across the university who would be managing their sections. This was valuable lesson. 

I moved on to another university which was pioneering distance learning. As a digital-first campus, I was exposed to a nascent CMS, digital marketing trends, and various coding and technologies. It was a formidable learning curve. When the university was bought out by a large EdTech company (and fired half of the staff and faculty), I seized another opportunity: negotiating my first independent contract with the parent company. They were in a bind, lacking both the institutional knowledge and the digital content expertise. From there, I had the confidence to negotiate employment and leverage my expertise.

Learning Inside & Out

I began my career inside organizations as the web editor/producer. I quickly became the internal champion of digital adoption and spread-headed the changes. I developed many skills alongside the growing internet and created a digital strategist job anew. While peers in agencies were provided digital frontend 101 training, I was self-taught and trained independently as the needs arose. Every new digital content requirement or technical challenge on the job was an opportunity to find solutions and grow my own professional talents. 

Digital content, back in the day, was considered the D-list role in Marketing and a necessary annoyance to IT. I frequently had to supplement resources by contracting with agencies and freelancers to build a website, run digital marketing campaigns, or upgrade a digital system. I learned from these talented agency pros. I regularly had to scale down their strategies, integrate innovations appropriately, and thoughtfully deploy techniques and technologies to match the organization’s resources and ability to maintain changes. Although working in-house, I pocketed knowledge and skills shared by external vendors. 

Whether paid as an employee or consultant, I have always been an in-house staff member managing daily digital operations. An agency (or freelancer) is hired to work for a short amount of time on a set project. My role is to maintain the website (and email marketing, social media, etc.) on a daily basis and curate long-term strategic plans. I have been a team of one supported by various vendors and sometimes part of a small office under the Marketing or IT departments. 

Big Content, Small Scope

I have worked for many organizations with volumes of web content to manage,  but employ digital experts episodically. Academic, healthcare, and government organizations have large, content-rich websites with hundreds of activities to promote; but they tend to have a short-term mindset and meager budgets. They will coast for ten years until falling so far behind on digital operations that the customer, a board member, or a new CEO forces them to get up to speed. 

If you are in a digital strategist role in these big institutions, you must do multiple jobs for years, making gradual improvements and advocating for upgrades—hoping for the day when budgets will increase or a digitally-competent leader will see the light. For many of us in digital staff positions in large institutions, the only chance to advance is to leave. And digital communicators are liable to be laid off during budget crunches. I’ve experienced this several times. At some point in our careers, most digital strategists are pushed into the contractor market.  

Contract-to-Perm Pipeline

Consulting has been an important rung in my career to stay current with the latest wave in the digital industry, which staid organizations often do not provide. However, the contract market is very competitive and extremely fickle (usually best when the economy is doing worse). Contracting is a temporary means to an end. Indeed, many of my permanent jobs came from starting as a consultant. 

I have been contracted by several large organizations to provide digital expertise in times of growth. When the project completed, I was converted into a regular employee to lead the digital operations. In other instances, I was contracted by former employers to manage digital projects because I had the in-house expertise (and they never filled my position). Digital professionals frequently move in and out of FTE and consulting roles, often with the same handful of organizations. Friends and colleagues inside the agency system typically seek mobility within their agency or move to another firm.