"Here Is My Problem" Volume #2

Hello, and welcome to my semi-regular “Here Is My Problem” column in which I will attempt to give my advice as to how you should deal with a professional problem. If you’ve got an issue with a person at work, with your career, or even with your life, I’m here to answer your questions to the best of my knowledge.

If you need help, please email me at ez@substack.com with the subject headline “Please Help Me.” Nothing I am saying should be taken as legal or accounting counsel, and if you email me with “Please Help Me,” that is your permission to publish your (anonymous) question. I love hearing from you and answering these, so please send them.

Two Jobs, One Conundrum

A lot of people are working multiple full time remote jobs during the pandemic (40 hours a week). These are professional corporate jobs in Tech, Finance and Marketing for large corporate clients. The argument is - if workers are now expendable - and labor is merely another commodity - why shouldn't one worker be able to treat their employer like a client and have more than one of them to offset the lack of security and protections afforded to us by arroding (sic) labor laws?

Is it unethical to work 40 hours a week as a contract employee and bill both employers 40 hours (80 hours total, more or less depending on your situation)? What are the limits to this arrangement? Should only contractors be allowed to do this? Should both employers be notified? 

This is one of those “it depends” ones. If you’re billing someone hourly and not working every hour on them, it’s hard to justify billing them a whole hour for that work. Conversely, I also don’t believe in snitching out workers to employers. I also add that I do not know the legalities here. Not legal advice etc., etc.

Ethically, if you’re billing hourly, you bill the hours you work. If the hours aren’t precise but the job expectations are, and you’re meeting them, who cares? Assuming you’re not breaching contracts or committing some crime, what you’re describing at that point is the classical consultant-contractor relationship. At this point, it doesn’t matter as long as nobody is being hurt or misled.

I previously wrote about people having two jobs and how it’s bizarre that the media hates the idea of two people working two “full-time” jobs at once, but adores people who are solo entrepreneurs who take on multiple contracts at once when in many cases, these are exactly the same thing. When I started my firm, it was just me with multiple contracts, which I worked on throughout the day. If I worked in-house for these people, I’d likely do the same thing, but if I worked two in-house jobs, that would be considered “bad.”

It’s all labels, man! But it comes down to the specific label you’re talking about.

Can You Fix Bad Company Culture?

I've been at the same company for 2.5 years - I started off in an admin role, and quickly picked up responsibilities and am now sitting in a newly created middle management role (our branch has grown from 7 to 25 employees since I joined, and we have doubled our revenue each year). As my workload has grown with the business, I've been able to hire a direct report and am in the process of hiring additional reports.

My own line manager is very much a traditional manager, who believes his job is to delegate and crack the whip. He was very skeptical when we all went remote that people would actually be productive instead of just milking the company dry, and had me implement a few annoying metrics to make sure people weren't slacking off (particularly when it comes to tracking our hourly employees)…the guy doesn't really show any leadership, and instead prefers to "let the team sort it out amongst themselves" when there are issues. Nearly every big decision he's made in the last 2.5 years I can trace back to a direct personal benefit to him.

As I'm building a team, I'm trying to do my best not to emulate what I've seen. I.E. I try to empower my reports to own things, give them autonomy, be super transparent, support as best as possible, make the hard calls, and generally keep our team structure as horizontal as possible. But I've not really got any good role models here as the larger ~250 employee business is hierarchical, bureaucratic, and frankly a bit anti-worker (we are private equity owned, which perhaps tells you everything you need to know).

I'm fortunate to have a decent amount of trust and autonomy, and our branch is the fastest growing and one of the highest performing in terms of revenue. So with all that explanation, my question: is it worth trying to change the company culture? Is it possible to use the responsibility and freedom I've been given to be a good manager for my team, and a good example for others in the organization? Or is it better to cut my losses and join a company where I'm not fighting uphill all the time?

I’ve said this before, but my father once told me that you learn two things from your parents - how to be a parent and how not to be a parent. I’ve taken this advice when it comes to management, in that you generally learn how to be a good boss from having a bad boss or a good boss, and the same goes for management. The problem is that bad management turns some people into monsters - people are bullied and hurt by managers, and take that to mean that when they have power, they can use it to bully and hurt others.

In your case, it seems as if you’re separated somewhat from your line manager, but you brought him up, which makes me think that he likely has a little more sway in your day than you’d like to admit. Regardless, your question was whether you can change company culture and whether it’s possible to use your power to make real change.

The answer is “yes, but how much time do you have?” You are not getting any younger, and I’m guessing by the fact that you have a line manager that you’re not actually in a position where real change will come anytime soon. While your branch may be the fastest-growing and highest-performing, that’s counterintuitively not going to guarantee that you’re appreciated. You could move to a new company and find that you’re in a similar boat, so make sure to use Glassdoor to evaluate these opportunities before you do so.

If you want to stay and make real change, what you’re doing is the right way to go about it. In my experience, the only thing that can overcome ass-kissery and office politics is being very good at your job in a way that’s impossible to argue with. If your branch is kicking ass and making money, keep doubling down on that - make them an example, and, most importantly, keep a systematic record of how you’ve done so. If you want to be a model for how the company could improve its culture, be that model - and make it clear how you’ve done it and how it worked. Stick to numbers. Private Equity loves numbers, even if they are evil creatures.

But…based on what you’re saying, I’m not sure you will change the company, especially as it’s PE-owned. As long as you’re there, do right by your people - and keep strong notes about your success too, so that you can move onto somewhere that doesn’t have a terrible culture.

Work/Life Balance

I've been with the same company for 20+ years and it's fine. The pay is decent, but the work is easy and my boss is on the other side of the world which means I can slack off for many hours each day (i.e. I'm bored). I also just got a pellet grill. Should I quit my job and alternate between going skiing (already bought my pass for this year), and trying out different recipes on the smoker? I'm only 52 so a decade plus from retirement, but have the savings to afford several months not working even if my wife would be annoyed. The two main things keeping me at my company are the insurance and the six weeks (plus holidays) of vacation I get each year. Who the hell wants to start over with that?

I, personally, would not quit, precisely because you said the work is easy and you can slack off. If your work is being done and your boss is happy, do not get rid of this job. If you’re bored, that’s fine - work is not meant to be “fun,” and if you’re slacking off for hours and have that time…go make some ribs, or a brisket, or read a book, or start a newsletter where you answer questions.

I am a cautious, anxious person and tend to find “I could” statements very scary. You could afford to take several months off…but what if things change in the future? What if your roof breaks or you have big bills or some other kind of horrible situation you didn’t predict, like another pandemic? I’m not saying to live your life in a constant state of fear, but if I’m honest, you seem to have a sweet position. It doesn’t seem like your boss is terribly demanding or that the work is hard, and you’re getting paid money for it - so keep doing it! Build up your savings so that when you do retire, you can really, really relax.

It sounds like your current work situation is ideal, and you’re not hurting or failing anyone by slacking off. So keep at it. Do your work, do it well, and keep that job. If you’re a decade from retirement, err on the side of caution. You get insurance, you get vacation time, and it keeps you busy. Bulk up those savings.

One thing I would really advise you do is take this email and talk to your wife about it. If she’d be annoyed that you quit your job to relax, you need to understand why that is and what her issues are with it. If she’s anxious that you relaxing would endanger your livelihood, that’s another reason you want to stay. Talk to her about this. It’s her life too.


If you enjoyed this, please email me your problems to ez@substack.com with the subject headline “Please Help Me.”