Madly in Love, Madly in Pain

Esther is a confused human being
4 min readOct 16, 2023


When I talked to people about my offer negotiation and relationship problems in my job, most people gave me advice that made a lot of logical sense but didn’t make sense to me.

I figured it was because, among all my friends, I stand at the top of the work addiction pyramid. Often, even their advice makes sense, but my madness on a deeper level isn’t taken into account in my decision-making.

If you ask my friends, they will most likely tell you that they are content with their work and have explored a lot because of the new freedom after graduation. But I only care about my work.

In addition, I have always thought that the daily life of doing passionate work would look like this.

But I don’t know why it somehow looks more like this now. I don’t know if it’s the nature of doing passionate work or if it’s just the circumstances I’m under. With my work, I’m either madly in love or madly in pain.

That’s why their advice doesn’t apply, even though everything they said is correct. They don’t have the strong emotional ties that I have. Their advice is like asking me to break up when I am already madly in love.

Due to all the challenges I have, I started to think if I should not accept this offer or accept it while starting to find a new job.

Luckily, I encountered two groups of people who helped resolve my inner conflicts:

  1. My powerhouse housemates.
  2. Experienced professionals.

My relationship challenge at work

My relationship with my boss wasn’t great; I felt constantly offended. When I vomited all my worries about my problematic relationship, a housemate reminded me, “It’s rare to find a job where you like everything, but it’s also rare to be in a place where you love everything except one thing. Learn to see the positive side of it.”

When he said that, I realized that even though my stars haven’t perfectly aligned, they’re almost there. I’m still concerned, but his comments gave me a lot of courage to try again.

After our talk, I felt understood. I no longer felt like I was the only one who had that many struggles and feelings in my work; there are still people here to share my determination and pain with.

My money challenge at work

If I accept my current offer, I will officially be the person who earns the least among my friend group. Many of my friends find it ridiculous and unfair. Initially, I was also conflicted because why would my passionate hard work result in a lower income? What if my passion doesn’t generate money in the long run?

I reached out to many mentors I knew to ask about this offer, and they all gave me the same advice.

“Don’t sacrifice enjoyable work for salaries. I think I made only x at my company, but I loved the work and mentorship I was getting, so it was totally worth it. Now I make 3x as much.”

They all asked me not to worry about earning now but three years later. They all prompted me to think long-term. As Patrick Collison said,

“Above all else, don’t make the mistake of judging your success based on your current peer group.”

Hence, I decided to aim higher than my peer group even if this meant an uncomfortable life and more risks.

The next big question one of my mentors asks is, “Strategies are all about trade-offs. When applying it to your career, it’s about what you are optimizing for.” After giving it some thought, I’ve decided that my current career priorities are as follows:

  1. Passion: learning x AI. I want it for the sake of generating lots of good ideas and niche problems for learning.
  2. Mentorship: Work with someone who I want to look like in 10 years.
  3. Hard Skills: Technical skills as an engineer.
  4. Soft Skills: Collaboration and persuasion skills.
  5. Building friendly relationships in the work environment: I still hope to have a lovely relationship with my team.
  6. Money
  7. Comfort

My current job scored strongly with the first criterion, so I decided to go with it. Even though I’m still scared that my learning in the startup will be able to translate to my next job or if I will not make lots of money pursuing my passion, I’ve decided not to worry about them for now. I want to try to make my passion earn a lot first. Only if it doesn’t work out will I go back to a regular job with good pay and a friendly environment as other people do.

Ending notes

Similar to a romantic relationship, I guess that today, if I’m not madly in love, I will probably not be madly in pain either. If my relationship with my boss sucks and I don’t really care, I can leave the work. I can work less. But because I want to work on my passion so much, everything that comes my way worries me 10x because it might affect my great work.

So I still decided to try it out until it didn’t work anymore.