Three events drove me to write these notes. First, my sister recently graduated college and started looking for a job. Second, I was invited to speak to recent grads at my alma mater about career advice. Third -- on further reflection, I wished that someone had given me this advice (or if they did and I was too hot headed to listen, I wish I had actually listened...) when I had been starting out.

So here are some thoughts:


On Getting a Job

Employers Looks For Practical Skills

You're looking for work, right? Well, there are is a tremendous number of employers out there that are looking for people to do work. The caveat is in the doing: employers need someone with skills to do very specific work.

Most small and medium-sized businesses (which is to say, the great majority of businesses)(1) are looking for people with practical skills to do specific jobs. These skills include: graphic design, writing code, balancing budgets, reviewing legal contracts, creating marketing campaigns, reviewing performance data, writing content, convincing potential customers to become actual customers, and so forth.

What there's not a lot of is: reading paper, writing essays, taking tests, debating the finer points of a strategy.

Moreover, employers are looking for specific skills to solve real and immediate business problems, and they tend to want you to have skills that have practice, a track record, and relevance within their industry.

Sometimes, this means you don't actually have the skills you think you have. Doing academic or desk research is very different from doing business research. Writing marketing content is really different from writing a personal blog or academic papers.

This also means that they're not actually looking for the skill in itself, but a skill that has helped deliver results in some way in the past. So if your resume can show that you used a skill to deliver business results (often profit or engagement or some other relevant metric), then you're 100 steps ahead of the competition.

The bad news is, most schools aren't designed as pre-professional programs and don't teach you 'relevant skills' (I'll write about that elsewhere). They're designed to foster critical thinking, preparation for an academic career, and/or other soft skills.

The good news is, it is never too late to learn a practical skill!

It's Never Too Late To Learn a Practical Skill

I graduated with a degree in Political Philosophy from a liberal arts college that drew on out-of-the-mainstream-in-the-US European philosophical and pedagogical traditions. In short, I was nearly unemployable when I graduated (2).

But, I also took a lot of classes in the school's integrated design and service design program, and these classes offered me the opportunity to work on real world problems with real world businesses and people (3). I took them mostly in my last year of college and they were by far the best thing I've ever done. I learned at the intersection of art, science, and business: how to make things, test things, and deliver results, from professors and class partners that worked in these fields as their day-to-day role. I learned skills that I use every single day. I learned how to do research, how to project manage a team to turn something from idea to reality, how to pitch a proposal, how to design and write convincing communications, and met smart and capable people that inspired me every day.

I also ran a blog while in school, with a number of different contributors. I wanted it to 'succeed' so I focused on readability and growing audience numbers, managing freelancer, figuring out how to be an editor, making sure the design looked good, figuring out some of the code-related to things to make it to what I wanted it to do. I also worked part time in restaurants to pay the bills, and learned valuable skills in customer service, dealing with people, managing expectations, handling things outside your control, and infinite patience.

All of these things, I levered into my first few different jobs in publishing, marketing, and digital content management.

If you're in school, that's the perfect time to explore a side project that requires you to interact with the real world in a tangible way. Do things yourself to start out -- it will force you to skills in design, technology, communication, and working with people.

If you're not in school, all of that is still true. A side project is the perfect vehicle for learning new skills. I learned how to code not because I wanted to learn how to code, but because I wanted to make my website do something I couldn't do without code. I learned how to use photoshop and other creative suite tools because I wanted to make my projects look good. In the beginning, I copied things and stole inspiration, and made bad and boring work. With enough practice, you go from focusing on how-to-actually-do-the-thing using your skills to accomplish what you want.

This process never ends. I recently learned how to do data analytics, manage AWS instances, and how to do proper accounting. Last year, I had to dive deep into learning supply-chain management, creating packaging, and how to do "sales" when I launched a business.

Job Hunting is a Numbers Game

Job hunting is ultimately a numbers game. The more places to which you apply, the more you'll hear back, and the more opportunities you'll come across.

My totally unscientific rule of thumb is "500-10-1". For every 500 applications you send out, you'll get 10 serious conversations, and one which will turn into something you actually want to pursue. Different industries and skill sets will net you different numbers, but the idea is the same: it's a funnel with a huge drop at each step of the process of application -> conversation -> offer.

Also good to note: jobs applications are often a black box of rejection. You won't know why you didn't get a job. Sometimes, people have biases against your name or your background or who you worked for previously or your age or your gender (even if those biases can be illegal). You just won't know. Other times, a role that you think you're a perfect fit for might be fake -- as in, it was created with someone already in mind but needed to be posted publicly in order to comply with regulations. (This happens more often than you think). Sometimes you'll have a great interview but the job will be offered to someone else because even though you're great -- they might be better or cheaper. Sometimes a company will post a job but then due to financial/internal politics/change of business requirements reasons that job will no longer exist, but the job posting will still be up because they forgot to take it down. Sometimes the application will be so popular that the reviewer will be overwhelmed with responses and you'll simply get buried and missed. Or you'll have applied too late because they already have someone further in the process. Or you'll be filtered out of a too-big pool with some rules of thumb that disqualify you based on credentials and keywords rather than skills and experience. You just won't know.

So the more you apply, the more you can make the numbers work in your favor.

The inverse of this is the type of people who applies to one job per month and tries to find the perfect fit each time. To make targeted applications work, you need to do a lot of research and find the right back door into the role. More on that below

You Can Hack the Application Process (To A Degree)

Besides applying everywhere and all the time, there are a few other things you can do:

  1. Use the Right Words
    Large companies tend to use keyword filters, because they rely on a) a few layers of people between the person who needs you and the applicant, and these layers who aren't as familiar with the requirements of the role, and b) they get a lot of applicants. Using the right words helps your resume get past the first stage of automated filters.
  2. If you write a cover letter, speak to the companies needs rather than irrelevant skills
    Companies hire to solve problems. If you can communicate how you can help them solve that problem, that's a leg up on someone who has interesting but irrelevant experience. Know your audience
  3. Design Your Resume
    The layout and readability of a resume ensures that whoever is reviewing it will either see the important information you need to communicate, or will get lost in the details. There's a lot of services than can help you craft a good resume.
  4. Find the Back Door
    If there's a job you really want with a specific company, don't try to go through the front door. Do your research on LinkedIn or the company site. Figure out whose area of responsibility that falls under, and reach out to them directly. Create a resume just for that job that highlights relevant expertise and gets rid of anything that would suggest you're better fitted for something else. Communicate familiarity with their work and how you can contribute. In short, find a way to stand out and do anything other than easy-apply to via a portal.

Take Weird Opportunities

You won't always know what you like until you try. Sometimes the opportunity you don't think you'd like turns out to be a great role.


Who You Work For

Big Companies vs. Small Companies

Working for a big company and working for a small/medium company are two totally different experiences.

In a small/medium company, you'll find that:

  • There is never enough time to accomplish everything
  • There are never enough people available and you'll have to do things outside of your area of expertise
  • ... and that's a great thing if you want to learn a wide range of skills and expertise
  • Work-life balance doesn't really exist and you'll probably work more than what the job description outlines
  • What you bring to the team/the work you do matters way more than your title or credentials
  • You'll feel that your contributions matter and make an actual impact.
  • You'll get to work across departments and across levels.
  • You'll probably feel underpaid and overworked

In large companies, you'll be able to:

  • Focus on specialized problems and practicing a skill set
  • You'll be well compensated with 401Ks, salary, medical, and vacation time
  • You'll have large teams supporting you and your work
  • You'll feel pigeonholed into a specific role and it's hard to grow out of it. A lot of people say they feel like a cog within a machine where their work doesn't make much of an impact.
  • Your title and credentials matter way more than the contributions you've made.

In short, small companies will encourage you to be a generalist, while large companies will require you to be a specialist.

There's a reason why this holds true in almost all cases:

When someone is just starting out building a business, it's just that one person doing everything. When new contributors are brought on, there's not really room for slack in the system: everyone has to pull a lot of weight. Someone who wants to do just one thing is either going to be not-a-good-fit, or brought on as a part-timer/contractor.

As as company grows and most core departmental functions (sales, marketing, operations, IT, finance, etc) are filled out, people running those departments will either a) need to scale their time by bringing on more people to do the work because there is more work than they alone have the time to do, or b) bring on specialized roles to fill in skills gaps. Often, a new hire will do both.

As a company continues to grow, these roles become more specialized and departments and hierarchies become less fluid. As individual contributions become more disconnected from the immediate impact of the business, the incentive structure and what counts as success in a role will warp. People will do the work that allows them to feel safe in their role. Politics over who gets what budget and who claims credit for successes will manifest themselves as department rivalries. People will do things that benefit themselves as opposed to benefiting the company.

Eventually, you become IBM, filled with ostensibly smart people but unable to run a business or deliver results.

I personally find it more rewarding (and quicker to grow) in small companies.

But large companies give you the benefit of easy name recognition on your resume.

Learn to Create Things, and Learn to Sell

Learn how to create things, and learn how to sell. If you can make something that has not existed before, you have created potential new value in the world. If you can sell that, you've actualized that value.


The Financial Stuff

Financial Freedom = Opportunities and Choices

Most people graduate college with debt, or take on day-to-day credit card debt. Other people simply have expensive tastes that dictate the need for large income streams. This debt will eventually close off opportunities to you.

If you have debt that you need to repay, you'll be severely limited in what you can do. You need to find a consistent job that pays above a certain threshold, and you'll need to hold on to that job until you either have enough savings, pay off your debts, or reduce your cost of living.

If you have no debt and a low cost of living, then you can do almost literally anything. You can backpack around the world. You can take on a job that's personally rewarding but doesn't pay too well. You can stop what you're doing to focus on learning a new skill or writing that book.

In short: the less you owe to other people each month, the less you have to work in order to fulfill those obligations, and the more you can spend your time doing things that benefit you directly.

Own The Work

There are two fundamentally different ways of earning money. The difference between them is the risk and reward that each one entail.

The first one -- the most common one -- is to rent your skills out. This is when you work for a set amount. Sometimes you're paid hourly, and sometimes you're paid a salary. But at the end of the day, there are two limits to how much you make.

The first limit is time. You'll be limited by how much you can make by how much you can work, and there's a hard ceiling there. You can't work more than 24 hours in a day, 7 days on a week. So even at max capacity, you hit a ceiling. But realistically, you'll get tired and want vacations. You can't work at max capacity without breaking and the harder you work the longer the rest you'll need.

The second limit is other people. If other people are setting your compensation, you're limited by what other people think you or your work is worth. You can switch jobs or get promotions to grow this limit, but there will always be a limit.

The second way to make money is to have an equity stake in the work. That's a fancy way to say, own a result of the possible profits of your work. If you collect the profit of your work, then there's no limit on the possible upside. If you're

The Personal Stuff

Ego is the Enemy

Build a Community


Footnotes

1 - Large companies, on the other hand, have internships and entry-level programs that train you for specific roles with no expectations of success. They also have recruiting departments that target certain schools and programs as a funnel into their career ladders.

2 - This was Eugene Lang College at the New School University, and the Frankfurt school of philosophy. I don't regret any of it, because learning things outside the mainstream gave me the tools to question commonly held assumptions and to think for myself and defend my ideas because no one in the real world would start from the same premises as I would.

3 - This was Parsons School of Design, also New School University