Down the rabbit hole

Noah Brown
5 min readNov 13, 2018

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If you’re looking for a job, internship, fellowship, program, or other experience that you think may be the next step in your career, but you’re not too sure how to go about finding the right “thing” for you, consider going down the rabbit hole. It is a technique I use daily and have been using for the past few years to bring some strategic structure to my fledgling career. Not only may you find that next “thing,” but you will also most certainly learn a tremendous amount in the process.

So what exactly does it mean to go down the rabbit hole? In a metaphorical popular culture context, the saying means “enter the unknown.” Perhaps unsurprisingly, for our purposes, it has the very same meaning. You will literally enter into the unknown by exploring what the internet and digital media have to offer. You will do so in a manner that follows no particular strategy other than merely following old, budding, or completely new interests.

You may be wondering how to literally explore what the internet and digital media have to offer…

1. Get inbound content

So, newsletters straight to your inbox. I don’t care what newsletters you subscribe to as long as they provide a constant stream of high-quality content that is ideally linked to other content. I subscribed to about a dozen newsletters in the onset and then narrowed them down to 2 daily (The Hustle and Fortune Term Sheet), 3 weekly (Accelerated, Fintech Collective, and AngelList Weekly), and a few other miscellaneous newsletters. The key is to only subscribe to content that you will read in full, otherwise, you are really just clogging up your inbox. It doesn’t matter what you read so long as you read content that you find interesting. For example, I found this peculiar bit from the Hustle particularly interesting…

Weird fashion trends in tech (the Hustle)

2. Switch your social media

Maybe you peruse Facebook a lot. Maybe you don’t. Maybe it’s Snapchat and Instagram stories that suck up your attention. Maybe it’s not. Whatever it is, ditch it. Start perusing LinkedIn instead. You will quickly find that the platform’s curated professional content is of significantly higher value to you and your career than really anything you will find on FB, Snap, or the Gram. Let’s make this concept an easier sell with the following image.

You can either listen in on a free webinar to learn about building a technology accelerator in an emerging market OR learn how to order Five Guys like a pro. You see my point?! Over time, spending more time on LinkedIn will translate into more targeted and exciting professional interests.

3. Follow the path

No matter where you start whether it be online or offline, trust that following the path will expose you to new opportunities. Here are a variety of examples of paths I have taken within the past few years that may spark your interest in going down the rabbit hole.

  1. A company comes up in conversation with a friend or family member. Later, I proceed to look up the company’s website, learning that they operate in an industry I had only recently heard of. The company is fairly small, so on the team page, I notice a variety of the employees are located in the Boston area. That’s my hometown, so I open up a new tab and search up the company on LinkedIn. From here, I peruse the full list of employees working out of the Boston office to see if I have any mutual connections. I notice there are a few with whom I have a mutual connection and one that went to my alma mater. Now I move over to the Jobs page and check out any open positions. There aren’t many openings, but according to the company’s LinkedIn page, they have grown 300% over the past 2 years. Something seems off, so I check their Crunchbase page and it turns out that they just raised $5 million this month. From this piece of information, I know that they will be posting a slew of jobs soon. I decide to reach out to that one employee from my alma mater to learn more about the company and inquire about future job opportunities.
    Company name → potential job opportunity
  2. One morning, I’m reading an article synopsis in my newsletter about the unique growth of a particular company. The article really intrigues me, so I click on the link to the full article located on Techcrunch. After reading the entire article, I click on the name of the founder that is linked in the Techcrunch article. The link brings me to her LinkedIn page where I can distinctly see her career path. She started off in consulting, which is something I had never considered as a career path. I click on a variety of the other high-level employees at the firm who are all located directly on the right side of the page. I notice that many of them also started off in consulting and are now in business development roles. This prompts to begin reading more about consulting as a first step in my career.
    30-second article synopsis → entirely new potential career path
  3. Late one night, I’m reading one of my newsletters from the previous day because I honestly forgot. I notice that one of the companies featured at the bottom just raised $12 million from an investor I have never heard of. The company, which makes an app for investing and money management, peaks my interest. However, instead of looking up the company, I look up the investor because they may have invested in a variety of other cool companies. I read a bit about the investor (an early-stage venture capital firm) on their website, as well as on their Medium blog. Their investment strategy seems interesting, so I check out the bios of the lower-level team members on the team page. Two of them seem to have participated in the same fellowship before working at the firm. So, I look up the fellowship. It sounds like an awesome opportunity, so I move over to LinkedIn where I look up past fellowship recipients. One of them lives in the town over from me at home. Using Hunter.io to find his email, I reach out to him asking to set up a coffee while I’m home over Christmas break to learn more about the fellowship and see if it’s the right fit for me. After having coffee, I realize the fellowship is a perfect fit and the fellowship alumnus offers to refer me.
    Random company → exciting potential fellowship opportunity

The concept of going down the rabbit hole may seem intangibly useful at first, but I can assure you that it translates into tangible results over time. I can attribute almost all of my internships (1 in Honolulu, 1 in Tel Aviv, and 2 remote) and other extra-curricular endeavors to voluntary online exploration.

“Don’t let schooling interfere with your education.” ~Mark Twain

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