Set low expectations at remote work

How To Set Low Expectations At Your Two Remote Jobs

Two keys to success while working two remote jobs is communicating and setting low expectations with your boss. You want to give the perception of meeting standards while striving to overachieve in your primary “keeper” job. You want to set yourself up for success, and by success, we mean keeping the two remote jobs as long as possible. Naturally, with working two jobs, one job will be more demanding than the other. The strategy is to set your effort low in at least one of the two jobs so you can navigate spikes in workload. Remember, the end goal here is to have dual income streams and reach financial freedom sooner.

Why Is Perception And Setting Low Expectations Important For Remote Work

We’ve heard it before, perception is everything. This HBR article illustrates a great example of how perception matters most at the end of the day, not the real story. The fact is if you’re perceived as a hard worker, it doesn’t matter what you do behind the scenes. In the two job game, you want to be perceived as someone who meets expectations. In reality, your aim is to do the minimum and get by: don’t get fired while secretly hoping to get laid off. A strategy to achieve a positive perception (and outcome) is accomplished by setting low expectations with your manager.

Why Setting High Expectations With Your Boss Is A Waste Of Time

Let’s first start by going over what everyone tells you to do – set high expectations, get promoted. Yes, this leads to more money. That’s great. But let’s look at the ROI because all great employees and MBAs should care about the ROI on behalf of the company.

But what about your Personal ROI’s? Indeed’s research concluded that the average employee raise is 3%. It may be a bit higher in tech, so let’s say 5 – 10%.

You might need to put in 30% more hours, more stress, more work to get a minimal increase in your salary. To me, setting those high expectations to get a promotion is a waste of time. You can get a second job and easily give yourself an 80% “raise” for your work. Also, I’m a good employee by being mindful of ROI’s – my own.

What I’ve Learned About Setting Low Expectations From Years of Working

What I’ve learned is expectations need to be set from day 1. I once worked with a new senior manager who always left at five o’clock since his very first day. New hires usually stay late to ramp up quickly. Not this guy. He set the expectation that he would leave the office by five and stood by it every day. It was genius. A year into the job, he still shut down at five while the rest of us kept working.

For managers, it’s typically hard to have that conversation, “can you put in more hours?” If your manager adds new tasks, just be clear you cannot complete them in the timeframe given. If you’re labeled as the “guy who leaves at five,” people won’t give you more work knowing you can’t get to it. More work is assigned to you once you do a great job, and it is an endless cycle. This story is just one example, but the lesson is to set expectations early and set them low. That way, the only place to go is up.

Once you set high expectations, you will always fail if you don’t meet them. Like the concept behind the HBR perception article, you can have done great work. But once you fail to meet the expectations, that’s what people remember. How many times have you thought you did a great job, but when you have your review, your boss mentions all the “failures” and missed expectations. Sound familiar?

How To Set Low Expectations At Work With Your Manager

Let’s get into how you can set low expectations while working your two remote jobs. As we mentioned, set these expectations early.

Be The One To Drive The Conversation

Don’t ask what your boss’s expectations are – set them yourself. Instead of going into the conversation by asking what their expectations are, set and communicate them to your manager. By asking what their expectations are, you are putting yourself in a corner. In developing your own low expectations and communicating them, you are placing the burden on your boss to have that difficult conversation with you to say otherwise. Psychologically, it’s harder to say no than to say yes. Let your boss be the one to say no to you. As a new employee, you’re most likely to slide by for the first review cycle with this method.

Communicate Often And Early

Being a great communicator can be a great asset. Think about those who do great work and are not great communicators. What about those who do mediocre work but can communicate. Who do you think will be looked upon more favorably? Set your expectations and make them visible to everyone to know what to expect. Take this as an opportunity to improve your communication skills. With practice comes mastery.

Example 1 Standard Comms.Example 2 – Overcommuication
Day 1 – “I’ll get Analysis 1 done by Friday.”
Day 5 – “Sorry, I hit a few snags in gathering the data, got busy with another analysis from Jennifer and I should have it by next Wed. “
Day1 – “I’ll get Analysis 1 done by Friday”
Day 2 – ” Just FYI – I didn’t Start on Analysis 1 yet, I was stuck on Jennifer’s report for a bit, let me know if I should drop it to work on Analysis 1″
Day 3 –“I started on Analysis 1, but am having trouble cleaning the data. It wasn’t as easy as I first thought (insert some details)- I met with Anna for some assistance (shows initiative) and got some good insights.”
Day 4 “This is taking longer than expected, I’ll give you an update tomorrow where I land.”
Day 5 – “Hey, I’ll need a few more days to finish, should have it done by next Wed. Here’s the progress we got to so far______ , what’s left is ______ ”
Overcommunicating gives the perception that you are on top of your work

As you can see from this example, the employee overcommunicating comes across as more trustworthy and in control. That’s the perception you want to convey. Even though something is not on track, or you haven’t started at all, just the fact you are communicating the details along the way makes people more comfortable. Also by communicating frequently, you can soften the blow of the miss.

Explain The Reasons Behind Your Low Expectations

While setting expectations is excellent, if you can back up your thought process to come to those expectations, you’ll have an even better case. Always come to the table with your examples of how you thought through your goal-setting process. For example, if you are new to a particular field, you can set small milestones to achieve “xyz” goal. With each milestone, you can explain how difficult it was to reach that milestone and drag out the timeline to the next set of milestones to achieve “xyz” mastery.

Good communicators always over-communicate. They are perceived to be in control, even though what’s said is the same message just repeated many times. If you have project updates, and the updates are the same for weeks, you’re still perceived as a good project manager since you are visible and proactive in communicating. Again it’s about perception. Like the deft hands of magicians, mastering resetting expectation is just as important as setting low expectations at the beginning.

Leverage Your Newbie Card In Setting Low Expectations

Being new has its advantages. No one knows you, so you start off with a clean slate. You can take advantage of this by setting low expectations with your manager for your first review cycle. There are many barriers to mastering your remote jobs, such as ramp-up time, company culture, new systems, and different procedures. Let these barriers shine in setting your low expectations, giving you all the more reason to have unambitious goals.

Leverage The Review Cycle 

Understand when the review cycle starts and ends. Set and time your goals to the review cycle. Usually, people set goals for the year, but keep in mind you’re evaluated on review cycles. There’s no use in setting goals for eight months when the review is only four months away.

Be A Follower Not A Leader

Realize that not everyone needs to be a leader in every job. Everyone is different and it takes employees of all types to make the company hum. There’s nothing wrong with being a follower and doing what’s expected. Remember, there are no leaders if there are no followers. Avoid the slippery ladder in your career. Take the side door instead.

Setting Low Expectations And The Two-Job Game Plan

The game plan for two remote jobs is to set the expectations low with your manager and prolong your hustle until your exit to another job or you’re laid off with a severance. For the second job, you’re there for one reason only: to collect a paycheck. A paycheck that is 500%+ more than a raise. The goal is to keep the paycheck going for as long as you can with minimal effort.

30 days – The first 30 days are easy due to ramp up but are critical to set low expectations. Set yourself up for success in working two jobs. Be that guy or girl who always logs off at five o’clock (even better at four), and let people know. Once you start extending yourself, answering emails and messages after hours, your co-workers will see that as the norm and more work will creep up on you. If you’re never available after a certain time, your colleagues won’t message you because they know you won’t respond.

60 days – In the 30-60 day window, you should set goals with your boss if that’s not already done. Drag out the newbie card and claim slow ramp-up time. Identify what absolutely needs to be done, communicate that as your goal, and meet them. Again, it’s all about the perception that you meet expectations, not the work you’ve actually done. You can do little work but as long as you met the communicated expectations you’re golden.

What If You Don’t Feel Right Low Balling Expectations At Work – Put The Ego Aside

We’re primed at a very young age to be the best we can be. We look up to leaders in society. If your ultimate end goal is financial freedom, you have to strategize and optimize for that and put your ego aside. You’re aiming to be a leader in your personal life and the truly ambitious ones land two jobs. Who cares if you’re not a leader in the public eye of a workplace? You can channel the guilt, if any, towards donating the extra money to a good cause, like the YMCA. Go do something you care about. Work is just a means to an end. Join us in the counterculture on the future of work.


  1. If you write code for a living, maintain a personal generic code library as a template for your deliverables. API functions are pretty much the same across companies. This strategy means that you can deliver quality results without putting in many hours. I pursued overemployment out of boredom. I have ADHD, so I ask to work from JIRA tickets instead of meetings.

  2. In the long run, how does one report dual / dueling full-time jobs on your resume when you’re looking for the next job? What do you do if, years later, your manager at B sees your resume describing that you were at job B during that time period? Seems too clever by half.

  3. I see overcommunication happening all the time! In a weekly meeting with 20 people in attendance, at least 50-75% are overcommunicating in a given week to mask the fact that they are doing very little actual work. It’s almost laughable. The #1 piece of advice I would give Millennials, is to learn how organizations ACTUALLY work, rather than how managers tell you it works. Once you figure it out, it is very easy to use that to your advantage. It’s way more common than managers think it is.

  4. This is so helpful and ensured me I was on the right track!

    I left government work back in May to join a small startup — I was overworked, doing the job of 2-3 people without the pay increase, and overwhelmed, without the ability to take a breather — all because I mistakenly was a volunteer/high achiever/over-communicator.

    My last two months in govt, I began working the at the startup simultaneously, its just as inefficient as the govt. I set that low expectation out the gate and it worked fine, the money was amazing. I now feign ignorance to many processes or areas of work, no longer volunteer for tasks, or stay past core hours.

    I saw the Overemployed article in Forbes recently and am now embarking on another remote, full time gig!

  5. I think you can still have high expectations at both, I still won awards and recognition at Job A while Job B took 75% more of my time and paid more…. thought it was funny. It is all about buzz words, like being LEAN. Just be “obsessed” with LEAN and say things, like can we use the project board instead of meetings, put me on stand by for a meeting if there is a specific question. Otherwise I am out (working on Job B). Other key thing for me was to communicate in Value and not hours, and focus on deliverables and don’t screw it up. Say I will get you X by Y and always nail it (except for roadblocks). If I got grilled on hours, I would be blunt and tell this story. Your check engine lights comes on, and you take it to two places, both with 5 stars. Place A says 500 bucks, drop it off all day and get it later. And Place B says we see that all the time, come in during your lunch break and will knock it out, will be 500. What place would you chose? You go with the convenient pro. When you deliver solid quality, on time, on budget, people will not watch or hover over your hours. People need to pay people to get stuff done, not micromanage. Glad I found this pages, been at this for 7+ years. The easiest way to work multiple jobs is to not suck at what you do.

    1. I’ve have job A and the company is an undisputed leader in their space, but I quickly realized that the job took me maybe 10 hours per week. Oddly enough, they love me and think I’m doing wonderful work. I start a second job soon, mainly to try it out but I truly hope this is a 3-4 year window where I’m not only just collecting paychecks, but also doing my job(s) really well. I have no intention of just coasting. So, we will see.

    1. Ha! When GM begged money off the government to stave off bankruptcy only to offshore manufacturing, and close American plants and fire workers only to reward themselves with raises and stock options, they’re lauded as geniuses not cheats.

      A handful of workers work two jobs and eVeRyOne LosEs tHeir MiNDs?!?

      Are you kidding me?

    2. I agree this is the stupidest article I have read in the last 20 years this just sets the president for more laziness which we already have enough of… What the hell is this be a follower not a leader what the hell is this who even thinks up this s***???

    3. Bruh, even stock photos show people doing two jobs now (just scroll up). And you’re telling me this isn’t legit?

    1. Over time slowly ‘remove’ those high expectations. As an example if you set the expectation that you will respond to emails/messages after hours stop that expectation (Good time is after a week of time off). Allow time to go by then stop another expectation. Doing this over a long period allows the reduction to go unnoticed. Another way is to ‘let’ co workers take some things off your plate, works best if your higher on the ladder and have some younger eager co workers.

    2. I did it a few years ago. I had developed an anxiety issue, I think I was on the way to a nervous breakdown. I had put in for a transfer, but my boss “couldn’t let me go”. I was apparently SUCH a good worker.

      I decided I would cut back on one task a week. Something that I did extra anyway. At the beginning of each week I selected something that I usually did on a volunteer basis, and decided I would NEVER DO THAT THING AGAIN. Whenever it came up, I would simply not accomplish it anymore. Just not. Beginning the next week, I picked another thing that I just would never get done. Every week I selected one more task I would never do again. So there was more and more of the extra tasks each week that other people were having to take care of. I walked around making comments about it to everybody “I’m so burned out.”
      , “I feel so tired all the time.”, “I’m just so exhausted.”

      After about 8 months, I was not such a stellar employee anymore. I put that transfer in again and my boss didn’t block it, in fact she said “It’ll be a relief to get rid of her.” Best move I ever made. I used that job to springboard me to my dream position, which I eventually retired from.

    3. ^^ what Mr. Pinkness said.

      I successfully ratcheted down my Job A expectations after it went remote. Most managers just delegate and nag people; if your manager doesn’t understand what you’re doing, that opens the door to make your work seem a lot more difficult than it is. He (I say that because it’s almost always a he who is in this know-nothing do-nothing situation) won’t want to look even stupider by pressing for details, so you should be able to keep the charade going. All of the great expectation-setting and over-communicating strategies in this article can be very effective at resetting expectations.

    1. We don’t discriminate. If we could’ve done it earlier or thought of it, we would have to be honest. However, that didn’t happen, so we “specialized” in our one job and now we’re rare enough skills to pull this off with multiple job offers. You alone need to decide what’s right for you with an open mind and weighing both sides of the coin.

  6. This is exactly what I thought, except I can’t write this well in English.

    I doubled my income by taking government contract on the side. Government is so inefficient, and I feel angry and happy at same time for taking tax payers money.

    1. Thanks Ant Tech for shedding some light on government contracting as another avenue to double our income! And I totally understand the conflicting feeling as I too was in government once. Told myself can’t hate the game can only play by its rules.

    2. Wow what was the government contract job if you dont mind sharing. Definitely looking into this my current skills are in data analysis and ecommerce.

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