sales and customer success

Journal: Sales And Customer Success – Mr.X#5944

The following is a guest post from Guild member Mr.X#5944 with some light edits. Check out more on this story on the Discord.  

Hello everyone! I’m Mr.X, a sales and customer success manager at J1 and J2. Both jobs are in enterprise SaaS. My only wish is I knew about Overemployed (OE) sooner. It has been four months now and I’m loving my newfound financial freedom.

My Current Pay: Sales And Customer Success

My OTE (on-target earnings) is $350K for 2022. I’m working 32-35 hours a week, which translates to an hourly rate between $192 to $210 whether I’m working or on paid time off. 

OE has led me to 4x my original income of $86K as a customer success manager.

This is my journal entry from four months ago when I first took a step towards OE and financial freedom.

A Week Before Starting J2

I must admit, I’m both nervous and excited. Nervous because I’m not sure what to expect, and excited for the same reason. What’s more, I’m excited about the fact that I’ll be able to become financially free sooner. 

Like most Americans, I live paycheck to paycheck. Even though I make a good amount of money from J1, I’m not able to save more than $200 (if that) per paycheck. And when an unexpected big expense comes up, it depletes my savings and I’m back to square one.

It just so happens my car decided to start leaking engine coolant today. If I had only one job, I’d be panicking. But the fact I have another source of income, I’m not as stressed. 

For context, my J1 currently pays me a base of $50,000 plus a monthly commission of $3,000. With J2, my combined base is now $107,000, bringing my monthly gross income to $8,900 before commissions. Here’s how I see it: the longer I OE, the more financial muscle I have to break away from the shackling of living paycheck to paycheck.

I also have a final interview for J3. If I get the offer, it’ll increase my total compensation to 200K+ with base, commissions, bonuses, and stock options. This is unbelievable.

Testing A New J1 Routine

I decided to do a trial run by starting my workday earlier for J1. I figured I may need to work 7-5 instead of my normal 8-4 when J2 starts.

I woke up at 5:30 am this morning and went for a jog to wake my brain up. I came back, took a shower, and sat at my desk by 6:45 am. I told myself I will sit at this desk and not move until all my work is done for the day. This is the first time I’ve tried this. Usually, I would spread my work over an 8-hour period watching YouTube and other creative ways to waste my time.

Now it’s 8:30 am and I’ve finished all my work. I’m now sitting at my desk to keep my laptop on and ensure my “productivity” doesn’t go down. Time to get that mouse jiggler and improve my tech setupIsaac’s note: this is the power of OE, it pushes your limits and you adapt to it.

After my experiment, I’m more excited now than ever to start my OE journey.

J3 Comes Knocking Two Days Before J2

I got an offer for J3. I’m now debating if I can do it. And if I can, will it be worth it

All three are spread between different time zones so I may be able to do it. Am I becoming Icarus? Am I flying too close to the sun? I suddenly feel like Damocles and how at any point this can all come to an end. Screw it. Let’s do this.

Day 1: Starting J2, Sales Implementation Manager

Today marks my first day being OE and taking my first step towards financial freedom.

Day 1 was surprisingly easy and light. J2 has self-paced training videos for me to watch during onboarding. And J1 has a light workload for the week. As of right now, I feel as though I can do this. Isaac’s note: always a good idea to take a week or two off from J1 when starting J2.

Week 1: Only Regret Is Not Starting OE Sooner

I’ve been 2xing for a week now and feeling great! I haven’t taken time off from J1 so I was nervous at first but I have been able to balance both workloads without any problems. I’m just mad that I didn’t OE sooner. Isaac’s note: no need to cry over spilled milk, look forward and go.

I’m excited that next week I’ll get my first double paycheck fromJ1 and J2. I’m finally making progress towards financial freedom. Time to pay down those debts and save in a massive way.

Week 2: Double Paychecks In Sales and Customer Success

It’s Friday. I passed out after work and slept for 10 hours. I was so beat! Honestly, looking back, I should have paced myself more and taken a week off from J1. It wasn’t really that hard. I got my first double paycheck and even though it wasn’t a full check for J2 (minus commissions), I still loved how I made an extra $1,300 for doing almost nothing except onboarding.

I’m loving OE thus far. Don’t let anyone else tell you that you can’t do OE in sales. It’s absolutely doable. All it takes is sitting down at your desk all day, emailing leads, and following up with people you’ve already spoken with. In fact, I think both sales and customer success are super-OE friendly. Isaac’s note: always job shop and try the job before you buy into it long-term.

Out Of The Matrix, Never Going Back

Back to the present day.

I have taken the red pill. I must admit, 2-3xing is easy!! I currently have four jobs all tied to customer success or sales. Sounds like a lot? To be honest, I can’t believe how easy this is. I’m lucky to be in sales where managers only bother you when leads aren’t being worked. Click the button, send an email, make a phone call. It’s that easy.

And honestly, you have 112 hours a week to get all four jobs done (minus 8 hours per day x 7 days for sleep). For me, 4x-ing my original J1 income and gaining financial security and better mental health is all well worth it. I’d run through walls to get my jobs done and get paid. Now onto my next goal, achieving financial freedom early!


  1. In addittion, just to refer that my J1 is updated in LinkedIn, so any change will affect one ofthe employeers. If i add a new section with J2 abd keeping J1 as active will sound the bells at J1, if i add J2 abd keep J1 below without end period wiill raise suspicions of daylighting. But besides social anxiety, in sales at least, we have also the time management issue as we scroll through forecast meetings and other meetings that may overlap between jobs that can only be performed mostly during customers’ schedules.

  2. I am currently working in J1 for 6 months and 15 days at J2. Both roles are at AE – Sales – SaaS – different customers and geographies.
    There is some pressure to update Linkedin from J2 to connect with colleagues, to activate Sales LinkedIn Navigator and i guess the pressure will rise after the onboarding process and start engaging with prospects. The tiyranny of being social active is creating too much anxiety and frustration because i want to try this experience for a longer period abd understand if i can make the figures and understand the sales cycle for j2. Besides, i am old school – all my experiences with lead generation through social media have been BS! I believe in calling and F2F or remote meetings and emailing. Probably i will quit J2 because i cannot accept the pressure due to the above. Is there any way to extend this experience and sort the LinkedIn and other anxieties?

  3. I’m currently a SaaS AE, and I’ve thought about getting a second job, but I wasn’t sure what to do about my job being on LinkedIn.

    How could I deal with not changing my LinkedIn if I pick up a CSM role?

    1. Hey SaaSAE,

      I’ve just started my new J1 and would start my new J2 within next few weeks. Luckily no one has yet asked me to update my current company (I’ve decided to not update my LinkedIn to my new company).

      Incase anyone does ask me to update, I would tell them that I’m not using LinkedIn anymore and was using it just for job search.

      I also plan on getting a J3, after which I would deactivate my LinkedIn for a couple of months just so I can tell anyone who asks about it that I no longer use it.

      Hope this helps and would love to hear what the OE community thinks about it.

  4. You must be pretty amazing at your job to be able to hit target across perhaps three different companies, every month. Juggling account management and the pipeline across 3 different CRMs would also be a nightmare I would have thought?

  5. Hi OE. New follower here. Can I ask for tips on time management handling 2-3 jobs all at the same time? I’m on the way to being hired by J2 and J3. And I’m both nervous and excited.

    Kudos to the team

  6. I have to start by saying I love this site. I visit daily for the next journal entry. I have been working the same job for a very long time and love the stability. I always wanted to 2X. I am concerned if I take second job, and either company finds out, I will be screwed. Are you concerned about the work number?

    1. Many people held multiple jobs in their past. TWN is not 100% accurate and relies on employers participating in its data-sharing scheme to simplify each employer’s own 3rd party employment verification process, like when you get a car or home loan. It’s overly emphasized as a “risk” — what’s risky is not diversifying your income and keeping your skills relevant. The world is changing fast!

    2. Additionally, TWN and other background checks only become an issue after you have a significant overlap and need to explain it to a prospective future employer (getting J3 or swapping one of your other jobs). It’s possible they could do a background check after a few months, but why would they? None of these third parties is going to rat you out sua sponte.

  7. I have enjoyed reading journals of the OE community. I need assistance with figuring out if anyone has come across a situation where their 2 or more jobs have the same payroll system (ie. Deltek)? I am nervous J2 will see an account already set up by J1 even though my log in information will be different on my end for both. If Isaac or the OE community could help that would be greatly appreciated.

    1. Agreed. You could have a cushy corporate job and be a part-time instructor at Lifetime Fitness. Maybe both use ADP. No one at payroll processors, benefits managers or retirement account custodians cares—those are third parties that handle very specific services for their clients, and that’s it. They couldn’t share information between clients if they wanted to.

  8. What kind if sales jobs do you have where you send an email and make a phone call? That gets you to your quota? Doubt it. This article is complete BS. Obviously not in sales.

    1. Mr. X isn’t in Sales but rather seems like a solution engineer/sales technical support in his J2 and in J1 an account/customer success manager. Just to be clear.

  9. This article seems to represent the opposite of “ Why Being Overemployed Will Save You From Overworking”

    Why send mixed messages about what OE is, or is this an attempt to be more inclusive of different takes on OE that would be more acceptable to the general population?

    1. Is making 300K over 32-35 hours a week the definition of overworking? I’d say no.

      I believe Mr. X was just making a point that 112 hours is the maximum workable hours, not that anyone should do that though I bet some poor investment bankers probably have. And if that’s what he’s willing to do to get ahead on financial freedom, who am I to judge?

      The OE philosophy is more about playing the long game and staying sustainable. Don’t do so much that your burn out and can’t recover. Your brain and mental health is your biggest asset for future income. However, it’s perfectly fine to ramp up and down your hours to fit your life goals.

      The point of OE is you’ve options. Do what’s best for you and Family Inc.

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