The Generalist’s Dilemma

The life of a generalist in the business world can be exciting. However, it also has its share of pitfalls that has been the bane of my existence from time to time. To best illustrate why, let me start with a little story. 

More than 20 years ago, I spent 2 memorable days in the city of Lucerne, Switzerland. It was spring time with perfect weather and mountain scapes coming alive with greenery. While I took full advantage of the experience, there was one thing I regretted…not buying a Swiss Army knife. 

In hindsight, this seems like a silly regret. But the Swiss Army knife is an iconic product that is legendary for serving a multitude of purposes all in one compact case. I’d imagine being the hero of the party when the corkscrew went missing. Or seizing the romantic moment of etching my sweetie’s initials with mine into a tree enclosed forever in a beautiful heart. 

Well, that time finally came this year when my son chose Switzerland as his destination for his graduation present! There is no shortage of sizes and design options. I opted for a more refined version that would fit for both fancy events and rugged, outdoor adventures. 

The Generalist (a.k.a. the MacGyvers of Business)

So the logical question you’re asking right now…what in the heck does all this have to do with being a generalist?

Similar to how the Swiss Army knife has a multitude of capabilities, so too does the generalist. By definition, the word stands for “a person competent in several different fields or activities”. In the business world, this can manifest itself in all sorts of employees or leaders. 

It’s the person with a B.A. in Fine Arts who started their career at a small firm as a marketing coordinator who transitions into a business development role and later becomes head of Product at a Fortune 500. Or a middle school teacher who earns their degree in Psychology becomes assistant professor at a local college and eventually launches an organizational development consultancy. 

These individuals pursue various positions while picking up multiple competencies along the way. It enables them to to see challenges and opportunities from various angles with the added benefit of seeing the broader cross-functional picture within an organization. 

The Generalist's Curse

Although the generalist’s diverse skillset makes them a uniquely valuable asset, this doesn’t make the recruiting lead’s job any easier when filling a role. They are usually looking for a certain years of experience doing a certain set of tasks well. 

Organizations are trying to be more expansive in their thinking.  This is evident as we see more job descriptions include a statement saying things like, “We know unicorns don’t exist so if you think you meet most of the above requirements, submit your application anyway.” Their intention is to try and find those diamonds in the rough like we generalists with transferable skills. 

Unfortunately, when recruiters oversee hiring for multiple roles with each receiving multiple submissions, the path of least resistance is to hone into the usual career specialist candidates. According to Zippia’s researchcorporations receive an average of 250 applications for each role! So you have to empathize for a moment with those whose responsibility is to weed through hundreds if not thousands of resumes. 

The Generalist's Game Plan

The task of finding that next dream role is daunting for the generalist. But it is possible if you develop and implement the right search plan.

Establish Your Personal Career Vision

An organization needs to have a vision for how its product or service will impact their customer base. This is the same for individuals. Having a personal career vision not only helps hone your energies on pursuing the right roles. It also provides a solid foundation for how you’ll communicate your value to recruiters and hiring managers. This is especially critical when your skillsets can be applied in a number of different functions. 

As a start, think through what you’re passionate about when you aren’t on the job. This could include community service, hobbies, leisure endeavors or day to day family activities. Amongst all these, think through the components that excite you.

Then, think through your work history. What are some of the responsibilities in previous or existing roles you enjoy doing most? What are skills that people often acknowledge you are strongest in?  

Once you’ve done this exercise, start drafting a personal vision statement. I say draft because you won’t necessarily get it right the first time and will need to revise. And be open to adapting it over time as new interests/insights come into view. 

Build a Target List

Now, you are armed with a vision to guide you towards the right career opportunities. The field of options will still be quite vast at this point though.

This is where you need to hone in on some basic criteria such as location (prefer to work remotely, hybrid or thrive in in-person roles?), workload (% travel, willingness to work across timezones, etc.), benefits and compensation.  Having these career guardrails in place can save you many hours in future futile searching.

Abandon, Explore & Refine

The next step can seem a little counterintuitive, but is critical for a generalist looking for a new career opportunity…forget your current or past titles…at least for the initial search. 

We often get stuck in the rut of pursuing roles with similar titles. However, the types of responsibilities assigned to a role vary by industry and organizational size. You could easily be missing opportunities if you are chasing a particular title in the beginning. 

Instead, start by deciding if you want to stay within your current industry. There’s nothing wrong with doing so, but I’d advise expanding the search. Even if you are a non-technical generalist, there are plenty of software companies that need your talents. Healthcare isn’t just for people with MDs or medical degrees. They need your marketing, operations or project management capabilities as well.

So jump on career sites like LinkedIn, Indeed and other job directories to start seeing what is out there. Their search filters enable you to input your career guardrails while leaving company, title or industry specifics broad. Spend at least a week performing this broad search to see what’s available.  

Make a list of the roles, companies and industries that are sparking your interest. This will enable you to find some consistent themes that will help make your search more efficient. 

Expand Beyond Recruiting

The reason all this work becomes important is the fact that it may take a lot of rejections before snatching that dream job. Zippia’s research states that, on average, it takes 21-80 job applications to get an offer. This is especially true when pursuing opportunities with hundreds of applicants. Forming your vision, honing in on your targets and then refining your role search is essential to help you be more efficient.  

However, the candidates who have the most success also extend their reach beyond then application Submit button on a careers page. Recruiters are just too busy to consider all that candidates have to offer. So you have to start searching through your network to find the hiring manager or people you know who are connected to the decision maker. 

LinkedIn is a great resource, but you need to work the system well. One of the obvious routes is reaching out to an existing connection that’s already employed at the company tasking for an intro to the hiring manager. Unfortunately, this probably won’t be feasible for most of the roles you are pursuing. 

So the next task will require you sending out an invitation to connect followed by an InMail message once accepted. You may also need to build connections with multiple new contacts just to get one that will respond.

Persistence is Key

The generalist career path can be challenging, but also rewarding if you clarify your vision, open your mind to different types of roles and expand your network. 

Feel free to share your questions, tips or anecdotes about your own generalist journey in the comments below! 

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The Generalist’s Dilemma

The life of a generalist in the business world can be exciting. However, it also has its share of pitfalls that has been the bane

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