Why I left my ‘Dream Job’

I’ve been meaning to provide more non-Meerkat, non-Hoover, and non-Product Hunt content. I want to share some things I’ve been thinking about lately as my life changes so much. Below is my first stab at this. I reveal some things I’ve never discussed before, and give my take on a variety of job-seeker topics. Your honest feedback is welcome.

TL;DR: These 2 Steve Jobs Quotes pretty much say everything:

Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle. As with all matters of the heart, you’ll know when you find it.
If you don’t love something, you’re not going to go the extra mile, work the extra weekend, challenge the status quo as much.

People have dreams/aspirations/goals in life, often times unrealistic or irrelevant to their professional success — but that’s the point of dreaming. “Aim for the stars” and all that. But when these ideas are focused on one’s profession, the concept of the “dream job” emerges. I have been fortunate enough in life to have found **made** my “dream job” twice already, at the ripe old age of 23. This may seem silly or contradictory, but in reality, dreams often change or even fade (especially once achieved).


Obviously, when I was young, I wanted to be a billionaire owning the first hotel on the moon (yes, this is actually something I recall telling people in grade school). I grew out of that, and as my interests narrowed, I knew what I wanted to do. Well, sort of. I went into college super-focused on business: I triple-concentrated (another contradiction) in Finance, Entrepreneurship, & Management Information Systems. Here’s how it broke down:

  • Finance — I’ve always been interested in the subject; I have a lot of family and know a lot of people in the field… While I knew I didn’t want a career in it, I still thought the fundamentals were important to know.
  • Entrepreneurship — Weird field of study. How do you “learn” entrepreneurship? I wanted to find out. I also love the topic and the world surrounding entrepreneurs, plus I’ve had a lot of entrepreneurs in my family. Seems like it’d be an interesting multi-faceted course load.
  • Management Information Systems — My true passion, the convergence of tech, data and business. It was a no brainer to have this on my resume, the classes were a little tough to bear, but I made my own way through independent study.

It’s a question often asked going through school “what do you want to do when you graduate? What’s YOUR dream job?” — I didn’t have a great answer for this. I always spewed the same combination of factors: “I love data and every company has data…” or “Something on the business side of a tech company, maybe with a startup” or “I dunno, something on the west coast.”

I knew the exact job and the title were irrelevant (more on this below) — what mattered to me most was the company I’d be at, the things I’d actually be doing, and the people I’d be working with. I found in discussions with friends and peers that my dream job was far more abstract than many peoples’. As I got closer to actually needing a job, things solidified and that answer became more standardized:

“A data-focused role on the business side of a small company, preferably in tech.”

This was the answer to my “dream job” in late 2013 as I got closer to my final semester in college.

So I found it at TWiT. I’d done my 2nd and final Co-Op (probably more on this subject later) at the company which turned into a year-long consulting contract and they really didn’t have a “job” for me… what they had were needs and problems that I could solve.

Random Rant

Titles are pretty irrelevant to me. At, TWiT I was a co-op, then a contractor/consultant, then a “Business Analyst” — in all my lead up conversations with our CEO Lisa, we never discussed a title. My initial offer letter didn’t even have a title defined. It’s a pretty minor part of the “job” — who cares what you’re called as long as you know what you do? Unless you’re in a client-facing/sales role, titles are purely a means of identifying position/rank, and shouldn’t be a part of the “dream job” philosophy. Once again, I didn’t know my title going into my job at Meerkat, I still don’t think it fully describes my role or my duties. I never say “I’m a business intelligence analyst at Meerkat” — instead I say “I do analytics and internal data work at Meerkat and also lead 3rd Party developer relations” — titles shouldn’t matter!

How I arrived at TWiT.tv

The brief version (who knows, maybe a longer version later) of how I ended up at TWiT involves my Leo-fandom from The Screen Savers days followed by me relentlessly emailing the CEO asking for a position as a co-op through Northeastern. It took about a year, but I made it. I was expected to sit at the front desk, run errands etc… until I started automating processes and talking about the business side of things. My role evolved, and I had to go back to school… but still worked for TWiT. I was getting closer to graduating and knew they were interested in discussing a full-time gig. It was less money than I was hoping for, it was in Petaluma (which at the time I didn’t really mind) and I already knew what I was getting into organizationally… But it was TWiT, and it was Leo, and I was excited and optimistic and maybe a tad naive.

For that version of me, the dream job had been acquired. I was working on the business-side of a small internet media company whose focus was tech. I was going to build internal data systems and automation tools. It checked all the boxes.

But dreams change. Reality sets in. However you want to put it… the dream job was not really fulfilling the dream anymore. A question one must ask themselves is which of those actually happened? Did your dream change? Did reality set in? The first exemplifies personal growth or a change in interest. There’s no mistake to admit. But the second basically admits a personal flaw. Maybe you thought the job would be something else, maybe you forced yourself into thinking it was your dream, maybe it’s pride-related and you couldn’t admit to taking a job that wasn’t a dream job… Who wants to come to the realization that they settled?

For me, it was definitely a mixture, my dreams changed a little, but that was overshadowed by reality setting in. I will admit when I am wrong, and I was wrong. Things were great, until they weren’t. This was actually pretty soon, ~5 months at TWiT. There were ups and downs, periods of bliss, followed by periods of misery. It was only once the frequency of the latter outpaced the former that I knew it was really time for a change. So I emailed somebody I had a lot of respect for and I thought would be knowledgeable and helpful on the subject. I had a plan. I had to find a new job.

But what was the early 2015 Jeffrey’s dream job? It was still very similar, data-focused, internal, business-related. But I was at a crossroads: did I want to look at startups?, did I want to try again for the big tech-giants? Honestly the idea of a startup seemed less scary to me. Not from the career perspective, but from the idea of moving on. I’d tried for the big tech companies (Apple, Google, Facebook, Twitter etc…) — they didn’t want me. It could’ve been my resume, my background, my whatever… but my concern was that they’d reject me (again), I’d be in a slump, and I’d end up just giving up and staying at TWiT.


I started meeting amazing people. I started being more open and public. I started sharing projects and ideas. I pretty much knew I wanted to work for a startup. A key driver in this was moving to SF, which I was going to do no matter what. It was an arduous process (hey, another topic for later!).

I spent weeks cultivating an audience and having fun while learning about the product deeply. In building MeerkatStats I learned the ins and outs of the data. I worked with the team, constantly providing feedback and support to the community. I knew it wasn’t my resume that’d land me a job anymore, it was my work and my actions.

So, I quit my job on a Monday, without a replacement lined up. I thought about consulting, trying to be be independent, but in the back of my mind I thought “hey, maybe Meerkat would hire me?” I knew I had to be free to find the next dream. Wednesday, I got a message asking me to come visit Meerkat on Friday and have a “conversation” with Sima Sistani (newly hired VP of Media at Meerkat)… that conversation really solidified that a role there would be a dream for me… I was fortunate that it ended like this:

Sima: “So do you wanna come work at Meerkat?”
Jeffrey: “Absolutely!”

We shook hands and I had realized my next dream job had been found. It was mine. I was ecstatic. In watching me on Meerkat and seeing the work I’d done with MeerkatStats, she knew what she needed to know. I truly think I earned this role. I had put in the work to understand the product and built not only a reputation in the community but also a valuable product.

Am I saying Meerkat is the end-all, be-all for me? Absolutely not. I thought my role at TWiT was my dream job for a short while. Right now, I’m extremely thrilled to be doing something I love for a company I believe in.

‘Dream jobs’ are a fluid thing. I don’t really think there is any one way to determine where you want to end up in your career. You may have an inkling of an idea, but grasping it or pursuing it too narrowly can only cause you to miss potential opportunities that might come around. It’s important to keep an open mind, it’s important to be willing to take risks, and it’s important to find what motivates you at each stage in your life and career.