Dear Businesslady: Time Is Money, but I’d Rather Have the Time

Photo by Luke van Zyl on Unsplash.

Dear Businesslady,

I manage the first and last mile for all of the new and most of the existing business for my company. I feel like most of the time I am doing two or three people’s jobs. It’s been this way for almost three years and whenever the management tries to hire someone to do any small part of what comprises the sum total, I am not part of the process and the person inevitably proves not to be up to the standard I have set. 

Even when I am at meetings or on holiday, I am inevitably passed into threads that need immediate assistance for no apparent reason other than that I am the senior person. It impedes people actually learning how to do their job; instead they are told (by me) again and again. I can’t stand it. My boss knows this, but thinks it will all work out organically. 

I am not sure. Even though I am only 38, I think that it is time to step back from the business one or two days a week. I’m scheduled to have a meeting about my compensation in the near future. I want to say, “Enough’s enough. Let me go down to four days a week.” Should I ask for less money, or should I say no raise for a period of time in exchange for fewer days a week? 

My mentors are terrible on this. I appreciate any advice.

—Too Good for My Own Good

Dear Goodness,

I’ve been looking forward to answering your letter ever since it hit my inbox. In addition to my ever-escalating evangelism for work/life balance, I have personal experience with the maneuver you’re proposing. And — spoiler alert — it may be a rockier transition than you’re envisioning.

Nevertheless, you absolutely can ask for this. But first you need to figure a few things out: what you actually want, how to maximize your odds of getting it, and what you’re going to do in the aftermath (whether you’re successful or not). Let’s tackle those one by one.

The Considerations

Right now, it sounds like you’re getting thrown into projects as a miscellaneous fixer, because everyone knows you’re good at your job and no individual person has to feel responsible for overburdening you. This is the risk of being a high performer: your work ethic fights with your burgeoning sense of burnout and you instinctively make yourself useful whenever the opportunity presents itself. Once your colleagues have learned how reliable you are, you can hardly blame them for — essentially — taking advantage of you. Correspondingly, no one should blame you for wanting to take a step back.

Ultimately, this will be a negotiation between you and your employer, and it’s always wise to enter a negotiation with a nuanced understanding of what you want: the in-a-perfect-world ideal outcome, the thing you’d be willing to settle for, and the whole range of options in between. Is “less work, less money” actually your best-case scenario, or would you be happier keeping your schedule the same, taking that raise you suspect is on the horizon, and establishing firmer boundaries over your workload?

You say your boss knows you’re frustrated, but “it’ll all work out organically” is not the response of someone seriously acknowledging a problem — and a problem with a top performer is a problem for the entire organization. Even more importantly, there’s a big difference between reducing your hours on paper and actually working less in practice. If it’s not actually going to be feasible for you to pull back, then your boss will either veto your proposition or agree to something that’s not actually sustainable.

As you’re preparing for this meeting, pay close attention to the things about your job that really bother you and assess them from all angles. The next time you’re copied into a days-old email thread that reads like the world’s driest epistolary novel, ask yourself what would actually make it less aggravating. If your colleagues would really be flailing without you, ignoring them won’t fix the problem. On the other hand, if you identify strategic improvements that aren’t directly related to your encroaching burnout, those will serve you well during the discussion with your manager. One obvious solution would be to insist that you be part of the hiring and training processes that you’re currently — absurdly and counterproductively — being left out of.

The Conversation

The good news is that you’re making a lot of valuable contributions, which means you probably have a decent amount of bargaining power. You cannot let your exhaustion or your empathy be your enemy. If you undersell yourself, your organization will eagerly accept your lowball offer. Don’t preemptively talk them out of giving you a sweet deal just because it seems unlikely. Right now you might be willing to trade anything for a shorter to-do list, but that impulse isn’t going to serve you well a month from now.

While you want to be prepared for a negotiation, I think you’ll be best served by treating this meeting as a conversation about how to make you happier at work. Start by summarizing your frustrations — calmly, succinctly, focusing on the big picture — and then Stop Talking. Try to do a LOT of not talking. (I say this as someone who struggles with silences, so I know it can be tough, but persevere.) Pausing lets your boss weigh in, and that in turn will help you assess how sympathetic they are to your situation.

Realistically you’re probably not going to get both the raise AND a reprieve from being everyone’s problem-solver. But if that option is even remotely on the table, you want to make sure you don’t knock it onto the floor by immediately launching into “I’ll gladly take a pay cut.” Every organization is trying to save money and that’s a bell you can’t un-ring.

A more plausible scenario is that you have to give up the imminent raise, but get relieved of the extra two or three people’s jobs you’ve been doing. Or maybe your manager will have other ideas you haven’t even thought of. Or, sure, maybe the salary reduction ends up being the only way to reclaim your time. Whatever arrangement you come to, make sure that you’re satisfied with what it means for your workload going forward. Make especially sure that it includes a concrete plan for explaining this new reality to your hapless colleagues and training them on how to fend for themselves.

A decent manager will find a way to keep you on their team, but if yours is committed to the status quo, then you might try to escalate this to whoever’s above them in the office hierarchy — provided you already have a decent rapport with that person. Ideally you’d do this in a way that’s not adversarial toward your boss (e.g., if they say “I don’t think the COO wants anyone on a four-day-a-week schedule” that’s an opening for you to ask “do you mind if I talk to her directly?” or else casually work it into a routine conversation with a higher-up). Remember: your manager is responsible for retaining star employees. If they’re unwilling to intervene on your behalf, then they’re failing to do their job properly. (Hmm, sounds like another instance of you doing someone else’s work, only this time it’s “retaining yourself!”) When someone’s neglecting their professional duties — and making your life miserable in the process — it makes sense to speak up to someone with the authority to address it.

Of course, the possibility remains that you’ll get some variation of “this is how it is and it’s never changing.” Bummer, but I think we all know your next move from there, and it rhymes with “heart cooking store a blue blob.” (Sorry, it’s just that I say it so often I feel like I should mix it up once in a while.)

But for the sake of giving you comprehensive advice, let’s assume that you’ll finagle yourself some kind of relief. What then?

The Consequences

Unless your overlords surprise you with their generosity, you probably will end up relinquishing some hypothetical income as part of the bargain. And man, some people get weird when they see you rejecting our culture’s relentless narrative of Success Is Defined by Increased Income. (Maybe that’s why your mentors are reluctant to cosign this plan. Or maybe they’re just jealous that they didn’t think of doing the same thing when they were younger, who knows.)

I do understand where this comes from — almost everyone wishes they had more money, and an intentional pay cut can read as “well to me, money is MEANINGLESS and I scarcely notice its absence! I’m literally the guy on the Monopoly board!” When of course that’s ridiculous, because your time is valuable too, and a bonkers work schedule often means paying other people to do the things you could handle yourself if you had the bandwidth. How is that objectively better? You sacrifice investment in your own life for investment in the company. That might be fine for some people, but it’s clearly not right for you.

Anyway, if you do encounter any jealous or otherwise awkward comments, just remember that they’re actually about the speaker’s complicated relationship with their own labor/compensation, not about you. Then change the subject as blandly and quickly as possible.

But minor social strangeness is not the biggest concern about this brave new world. What you really need to watch out for is… not actually reducing your workload at all. There will be a chorus of “oh but you used to help with,” myriad folks mysteriously incapable of expanding their skillsets, and a never-ending parade of supposedly extraordinary crises that require your assistance “just this once.” Don’t let them wear you down. Get used to saying things like “sorry, this is actually a question for [someone else],” and “I’ll get this back to you by [timeline that’s actually manageable for you versus the quickest possible turnaround].” Your expertise will surely be missed, but that’s okay. You’re basically taking all of your accumulated misery and spreading out evenly among the rest of the office, which seems pretty damn reasonable to me. Your coworkers will be able to deal.

However, even if your colleagues are completely respectful of your readjusted role, you yourself will probably feel a bit uncomfortable at first, unable to shake the sense that you’re slacking. Push through it and establish boundaries no matter how wrong it feels — I promise it will fade eventually.

I had a hell of a time adapting to a shorter workweek, and the thing that finally helped was creating a spreadsheet to track my hours. I had no trouble working way more than I was supposed to when the job required it — and I’m salaried so this is as it should be — but I felt guilty pulling back when things were slow. Seeing an actual tally of “X hours over” lets me know that I’ve earned a bit of a break, and after doing this for a few years now, I’ve learned to trust that my work ethic is never going to atrophy. Trust that yours won’t either.

In fact, you’ll be better at your job when you’re not stressed out and perpetually overwhelmed. More importantly, you’ll be better — much better — at enjoying your life. I think a lot of people would benefit from having your perspective, and I hope this is the beginning of a beautiful new chapter in your career.

P.S. It’s good to be back, Billfolders! Sorry for the long lag between columns — I was consumed by work, travels, and fat coughs.

In honor of dearly departed blogs The Awl and The Hairpin (which, among so much other goodness, introduced me to the rap prowess of Dominique Young Unique), enjoy the NSFW query that kept running through my head as I wrote this.

Courtney C.W. Guerra has been writing Dear Businesslady since 2014 and is the author of Is This Working? — a “witty and entertaining” career guide for people who don’t think they want to read one. Keep in touch via TwitterFacebook, her TinyLetter, or her website. Need advice? Email

Read the Dear Businesslady archives on The Billfold (and when it’s back online again — which should be soon! — The Toast).

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