Dear Businesslady: Why Do Anything?

Four considerations for professional decision-making

Image via Justin Lynham

I’ll be back with a Q&A column next month — submit your questions here! In the meantime, I have some overarching career advice.

It’s a rare and exciting thing to encounter a piece of genuine wisdom, and even more so when it comes from an unexpected source. I was inspired to write this piece after watching The Wrecking Crew, a fantastic documentary about the decidedly unfamous studio musicians who performed (and in many cases helped write) some of the most iconic songs of the 1960s.

While the entire film is worthwhile — and thought-provoking in its revelation that the music industry used to be reliant on largely uncredited creative labor — a particular moment hit me with cartoon-lightbulb intensity. About a third of the way through, you learn that guitarist Tommy Tedesco would only take a gig for one of four reasons: “for the money, for the connections, for the experience, or just for fun.”

I’ve been thinking about this rule ever since, impressed by its insight. For all its self-evident simplicity, it can adapt to accommodate the complexity of any professional situation. Every side gig, every position, every career path is dependent on the interplay between each of those four factors.

Let’s break it down.

The Money

If you’re talking about a J-O-B job, then some kind of compensation should be a part of the deal. But not all payments are created equal. Even if you’re being offered “good money” for a particular kind of work, that doesn’t necessarily mean it’s going to be worth it to you. You have to consider the time investment involved, the way it aligns with (or disrupts) your larger goals, and the imposition it would entail — which, within this framework, we might call “anti-fun.”

Although everyone has their price (as the saying goes), everyone also has a limit of what they can tolerate, and it’s important to listen to your instincts when it comes to the latter. All too often — especially early in your career when the idea of meaningful compensation is still somewhat of a novelty — it’s easy to focus on the numbers after the dollar sign at the expense of the labor leading up to it. More money is always better, sure, but that’s only true if the work itself is reasonably agreeable. If you don’t need the bigger salary of a more demanding job, or a time-consuming freelance gig, or some overtime pay to offset a lost weekend — if your budget can survive without the extra income — there’s no shame in saying no.

Do it for the money, but only if it’s actually worthwhile. Your calculus will have to include the other three reasons that follow; a low-paying (or volunteer) position might have other benefits that balance out the financial drawbacks.

The Connections

In the white-collar world, this dimension is closely linked to “experience,” with a few distinctions. For some jobs, the work itself might not add much to your resume, but it will put you in contact with people who can offer you more meaningful opportunities down the line. My own career has benefited from this kind of productive proximity on a couple of occasions: higher-ups realized I had abilities beyond my job description, and that meant I was in a better position to pursue promotions.

At the same time, though, this route to advancement is never a guarantee. You have to be willing to ride out the job you’re actually being paid to do — for however long you’d typically stay in that role — in order for the long game to pay off, and you have to be willing to walk away if your opening never materializes. It’s possible that your workplace or industry will shift around such that your well-cultivated relationships won’t bear fruit for years and years, if ever. Going into a job with the attitude of “I’m just slumming until y’all recognize my greatness” is likely to have the opposite effect in terms of building a useful network.

Do it for the connections, but be realistic — don’t pin all your professional hopes on a few well-placed people.

The Experience

This factor seems even more relevant to the professional world than the music biz. I imagine that if you want to hire a musician, you can get almost all the information you need from just listening to them play — and if you like what you hear, you don’t necessarily care how much background they have in a particular genre or style.

By contrast, hiring decisions for office jobs typically rely on self-reported experience instead of skill demonstrations. Beyond the entry level (where applicants need to present a convincing case for their hypothetical abilities), your professional prospects are largely defined by what you’ve already done.

In practice, this means that a few uninspiring positions can become more than the sum of their parts once they’re aggregated into a single work history. Any time you apply for a job, you’re telling a story about how your particular profile will meet the organization’s needs. Whether you’re deliberately developing expertise in a specific area or ambiently accruing proficiencies as you move up through the ranks, you’re constantly adding new qualifications that can be deployed on future resumes and cover letters. Even seemingly niche skills can be transferable across industries with the right framing, which means that every position has the potential to advance your career. The key is to keep track of all your accomplishments so that you can use them to market yourself to new employers.

Do it for the experience, and remember to present that experience in the most compelling way possible on your job applications.

The Fun

Okay, so a lot of office jobs aren’t exactly fun. Plenty of musicians will pick up a guitar just for the hell of it, but I’m pretty sure no one does data entry as a soothing downtime hobby.

Still, once you adjust for the “it’s work” element, there are usually some fun-esque aspects to a job: interesting and likable coworkers, challenging and engaging work, and so on. I’d put passion within this category, too—if you’re supporting a cause or organization that’s important to you, it’s easier to endure the less glamorous parts of a given position. Things like convenience and other side benefits are also relevant here — if you’re getting valuable perks, or have an effortless commute, that factors in to your overall job satisfaction.

If you truly hate going into work, that’s probably a sign you should be pursuing other positions — unless you’re getting enough money, connections, or experience to balance out your arduous daily grind. And if your options seem painfully limited, that means it’s time to start thinking about a possible path toward something more enjoyable. Sometimes you don’t have much choice in terms of the jobs you take, but keeping those considerations in mind will at least help you nudge yourself in the right direction.

Do it for the fun, to whatever extent possible — don’t sacrifice your own happiness on the altar of professional advancement.

A Piece of the Pie

Under Tedesco’s philosophy, you ought to evaluate the four components above before making any decisions that affect your career. Imagine them forming a pie chart: if they combine to create a complete circle, then that’s a position worth taking. If there’s a gap between one wedge and the next, then proceed with proportionate caution — and if a slice is essentially missing, then you’ll probably be better off doing something else (whether that means turning a job down entirely or planning to decamp as soon as possible).

The ideal proportion of these factors will vary across individuals and industries, but if you want to be a reasonably happy member of the workforce, you need to figure out some kind of balance among them. And given how complicated professional choices can be, it’s incredibly useful to have a rubric that breaks them into manageable parts. In the end, I suppose it’s not surprising that a musician would come up with a brilliant metaphor for bringing four distinct, crucial elements into perfect harmony.


Businesslady is in her early 30s and somehow managed to find a rewarding career despite her allegedly useless degree in the humanities. Her job history includes everything from food service to retail to corporate nonsense, but she currently does writing and editing for a nonprofit, and devotes the rest of her life to playing video games, patronizing bars, and spending way too much time on the internet (including but not limited to Twitter). Her career guide, Is This Working?, is forthcoming from Adams Media in March 2017.

In need of workplace advice? Email me! dearbusinesslady@gmail.com

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