How to pick the right job

People often ask me how to pick the right job. Since its the beginning of the new year, this question comes up more often. In that spirit, I decided to put my thoughts to paper to share for everyone.

Most people will tell you to pick an industry and pick a function/role and from there apply to companies. Using that matrix you can determine where you should apply. If you’re looking for a career change, many folks say it’s easiest to switch industry and stay in the same function, a little bit harder is to switch function in the same industry (this presumes you possess some subject matter knowledge of the industry), and the hardest is to switch both (understandably, as you’re a risk for the employer).

My take on it is this: Find the subject matter you’re interested (in tech the big trends at the moment: AR/VR, Big Data, Machine Learning, Blockchain, and IOT), find an industry you’re passionate about (healthcare, finance, retail, industrials, advertising, etc), and find a use case worth spending your time in (in tech that could be advertising, analytics, business process optimization, e-commerce, SaaS, enterprise tech, etc). As long as you’re hitting those 3, a role (which often varies from company to company) will emerge.

The Framework:

Find the subject matter, industry, and use-cases that you’re most passionate about

Finding each vertical, let alone a cross-section of these three dimensions is hard. The first step I recommend is doing some personal self-reflection.

Step 1: Self- Reflection

Figuring which vertical you’re interested in each of the three dimensions is hard though. This requires a lot of introspection. When I reach a point in my career where there is a pivotal step, I always ask myself three questions:

  • What are you good at?
  • What do you enjoy doing?
  • What are you passionate about?

What are you good at?

This really gets to what do people recognize you for; what are the hard and soft skills people admire you for. Reflect back on the time’s people have given your positive feedback, don’t just think professionally, think academically, and personally as well. What areas are the ones that keep coming up? Write those down.

What do you enjoy doing?

Being passionate about what you do is important. Think back to the times that you were truly happy when you were doing work. Was it project-based, team-based, thinking in isolation? Were you doing it analytical work? hands-on work? strategic work? Thinking through the type of work really helps with shaping what you want to do.

What are you passionate about?

It’s not just about the type of work you do, but its also about what you’re working towards. What are the topics or areas that get you up in the morning? Is it thinking about how to make things more efficient? Is it about building a new transformational product? Is it about making people around you lives better? All of these can shape what you do and how you do it.

Once you’ve established these three dimensions and written them all down, take a step back and see how these three look together. Perhaps you’re really good at doing analytical investigations, and enjoy working on strategic work, and are really passionate about creating stories. Think through all the roles that are out there to see what fits that mold (e.g. an ad agency executive). Can’t think of jobs. There’s plenty of job lists out there. One I like is the 100 jobs exercise. Normally, this exercise is meant to be done blindly without the self-reflection. Perhaps try doing the exercise before and after the self-reflection, that may shape what you think is a right role for you.

Once you’ve found those roles and jobs, start talking to people about those roles.

Step 2: Informational Interviews

I highly recommend performing informational interviews (I will write a whole blog on how to best do these later), with someone who has a role that is deep in one of these dimensions to see if this is a right fit for you. This will help you shape the role and pivot it to something that may make more sense, because after all you may not be fully aware of all the jobs that are out there.

Also, don’t hold yourself back with the thinking that you are stuck to these 3 dimensions long-term, they can keep changing with your career. As long as you’re passionate about it now, you can go deep on it and pivot from there, because you’re deep in at least one of the 3 dimensions.

After speaking with people you should begin to get a good idea of what role would be the right fit for you. The side benefit is as you start talking to these people, you start to build your network of people in the area that you’re interested in, which will pay dividends in both the short and long term.

Step 3: Finding the right size of company

Through the informational interviews you’ll begin to narrow in on an industry, but choosing the right company within that industry can be difficult. A lot of it can depend on your role and the culture of the organization.

One of the biggest things that shape culture of the company is the company size. Picking a small company typically means you’re going to be doing many different roles, you’ll have more autonomy, and be moving quickly. The downside is that there is more chaos, less security in what you will be doing, and you may not feel like you accomplished a lot on a day-to-day basis. Larger companies may feel overly bureaucratic, and you may feel like a small very specific cog in a very large machine, but your level of impact as an organization is huge. If you don’t know what size of a company is right for you, I subscribe to the Andy Rachliff approach of joining a rapidly growing company that has 500-2500 people (sometimes this can be a business unit within a larger organization – the food or digital teams at Starbucks). At that stage, the company should have a good idea about where they fit in the market and are bringing on people to help them grow. It should be growing rapidly (rocket ship level growth, where all eyes are on the success of the team). Your brand gets attached to the rapidly growing brand of the company, and you can see how the mix of structure and autonomy are being figured out throughout the process of this rapid growth. As a result, you get an idea of the stage of company you like (would you prefer more structure and mentorship, or less) and are informed about what’s need to grow an organization (one’s that stifled with bureaucracy, or what processes are needed to move more efficiently for a startup). This, along with your geographic preferences should narrow down the list to just a handful of companies.

Step 4: Finding the job

Now you have the handful of companies of interest and the right dimensions of what functional areas of businesses that are of interest. It comes back to a process of informational interviews. Tap back your informational interview network if they know people at the given companies you’re interested in in the departments you’re interested in. Network, network, network your way through the company to a role that seems like a right fit. Along the way get a sense of how that company works, what they like to do, and how you can fit into that organization. If a role is hitting all 3 of your dimensions, and you’ve vetted that the company is growing sustainably well (will write a blog on this as well), and you love the people you’ve interacted with throughout. Then and only then start letting them you’d be interested in finding a job in that area of the company. Don’t worry about titles. As Eric Schmidt once said, “If you’re offered a seat on a rocket ship, get on, don’t ask what seat.”



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