Can your boss be your friend?

NO! Please read this warning!

Freelancer's Journey of Love and Madness
Story Saturday
7 min readJul 20, 2024

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Photo by Andrea Piacquadio: https://www.pexels.com/photo/yelling-formal-man-watching-news-on-laptop-3760778/
Photo by Andrea Piacquadio

NO — A WARNING.

I’ve been working for 21 years. That, I think, gives me enough credibility when I tell you that your boss is NOT, NOR WILL HE EVER WILL BE, your friend.

You might say otherwise. You might say, “Well we’ve had different experiences. That’s an unfair statement!”. I respect that, I respect you. But hear me out and by the end of this, I may redefine your perception.

The Start Of Our Friendship.

Let’s call him, Buddy.

I’ve been working with Buddy for 10 years. We’ve gone through the roller coaster of a startup. My loyalty was unwavering. Clients tried to poach me but I stayed committed to him and the company.

He did reciprocate. At the time, I thought they were incentives, bonuses, and gratuity. I now know that they were manipulative tactics to reel me in.

We became close. So close that I treated him as family. I’ve never been the outgoing type. An introvert I am. He became a friend. So much that I’ve opened up to him on everything about what’s going on in my life. And I mean EVERYTHING.

How close, you ask? Well — so close that when I got pregnant (My husband and I have been trying for 5 years), he was the first one to know — not my husband, not my family.

So close, that when I found out I have ectopic pregnancy and needs to be terminated, he was the first one to know.

So close, that after surgery, I was in so much pain with things coming out of me, and I showed him all those as well.

Don’t get the wrong impression — I am very efficient at work. I waste no time and my goal is growth for the company.

Red Flags Everywhere.

I’ve seen them — I chose to ignore.

Multiple times where he’d fault a worker for not meeting the goal, when the worker actually did — he just either forgot about the target or changed it but did not advise of the change properly. Then he would gaslight and deny this change.

Multiple times when he would ask me to source out workers or interns and advise them that the compensation will be “exposure”.

Multiple times when he would terminate workers without prior notice with their last day as the day they were informed that we will not be needing their services anymore.

Multiple times when I’ve received follow ups from previous employees that they have not been paid yet for their last month of employment — and this was at least 2 months after ending their contracts.

I’ve seen the signs but I remain silent. I was still quite new to corporate — maybe I misunderstood the situation. Perhaps it was how things are suppose to happen.

And Then It Begins…

Fast forward to this year is when it all falls apart. Here’s the timeline:

At the beginning of the year without prior notice, the salary was delayed for a week. My follow up fell on deaf ears. I have incurred interests on my payables and missed my deadlines. When it finally came — there wasn’t even a single apology or explanation.

It happened again 2 months after. This time I got an explanation — “The client has not paid us yet”. In my head, I was thinking — Well, I don’t actually work for the client, I work for him — so my salary shouldn’t really depend on whether or not the company gets paid. I’m not a partner, or a co-founder. I work full-time, 12 hours, no 1 hour break — just straight grind.

To make it a little easier, I requested that my salary be credited in 2 parts. This is to compensate for the damages I am incurring. I got a written confirmation, that this can be done. The first part will be on the 23rd, and the second at the end of the month. My decisions thereafter was based on this promise. Wanna guess what happened next?

It was not credited on the 23rd. Instead, I got a poorly written email stating that he wouldn’t be able to do this because the client has not paid yet.

But the damage has been done. I’ve lapse on due and now I’m being sued for not acting on my promissory notes — A civil case is being filed!

I’ve written a lengthy note about this. I was in shambles. I pride myself for always being on time with responsibilities — and now, I’m being sued for not making payments.

It Continued…

The 2 months was calm — good news all around. Our projects are booming, and the new interim CEO is bringing in multiple new businesses. The greatest one came on the 30th of May — We have 2 new investors. I was told “We have 2 new investors and the delays before shouldn’t happen again.”

Things are starting to turn around. The future looks bright.

D-Day.

Photo by RDNE Stock project

We are winding down.

It has only been 2 weeks after the good news. What the heck happened in between? No one from the management gave even the slightest hint that things aren’t working out. We have new investors, and we were kept getting the news that new clients are coming in.

My mates and I were a wreck. But hey, this is a startup afterall — things are fast-paced. Maybe it didn’t just work out.

I started to send resumes and look for other opportunities.

The Assurance.

I was told not to panic. Pretty hard to do since I’m about to lose my job. I was assured that he has a colleague who would take me in and I will still do part-time work for him. Overall, my compensation would remain the same — I shouldn’t worry, he will introduce me soon as he already told her about me and she was actively seeking for support. He will make sure I am stable during this period.

I trusted him. I did not entertain full-time roles. I figured a part-time would suffice, since I’ll be working technically full time with him and his colleague anyway.

The Gaslighting.

2 weeks after our conversation, he then told me, he feels uncomfortable with me working with his colleague. I was taken aback. I reminded him of our conversation and asked what changed. He didn’t give a specific reason. Instead told me “I never really guaranteed”.

In the name of all that is holy, what the hell does that even mean?!

He also reiterated that the “PLAN LAST MONTH DID NOT CHANGE BECAUSE HE WILL STILL WORK WITH ME FOR AD-HOC TASKS”.

Excuse me?! — It did change! It changed a lot! I know will not have a full time role. I cannot survive with just a part-time post. He again told me “I never really confirmed the other job”.

The passion is gone.

Despite the anxiety of the situation, I’m still working as hard as ever. I have a lot of videos to edit, but I make sure to advise the messaging channel that I am focused on completing the remaining tasks so they know my responses maybe delayed.

It’s hard to be positive when you feel manipulated and lied to.

He said, I’m not responsive. I reminded him that I am working on edits and it’s hard to respond on messages when I’m in the middle of a task but I send a notice of what I’m doing at the start of the day and at the end of it. I’m not superman or the flash.

He waived this off and said my communications were not professional and I’m unresponsive. So I checked all my messages and didn’t find any “unprofessional” ones.

He said, this is very unlikely of me and with all the years we’ve known each other, this is the first time, he’s seeing me like this.

Well… It’s hard to stay all-jolly when you kept getting gaslighted, innit?

Breaking Free.

He now has a new client — and he said he will bring me to full-time again “Soon… maybe this week”.

No more. I am done.

Your boss is not your friend. He will never be. He is there to look after the interest of the company and in the process provide feedback and help an employee improve.

My mistake was blurring the line between personal and professional. I became too attached to the work and the people so now it’s more painful — like being betrayed by family. My emotional connection to this company has weighed more than it should have. I’ve given my entire life to this team. My heart and soul. So this is hurting me more than it should.

Learn to establish boundaries. Respond warmly but create distance.

Keep it cordial — and always have a backup for yourself.

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