Go back to school vs learn on the jobBy @ryantmcknight | Posted: June 06, 2015
Measuring the value of any particular personal goal is a task best left to the individual. Although it is often immensely difficult, you can evaluate a goal and compare competing goals by determining the extent to which each one aligns with and furthers your core values and helps satisfy basic human needs.
Some research from social psychology suggests that goal/need alignment is “associated with more positive…performance and well-being outcomes.”  No surprise there.
A form of this logic helped me determine it was in my best interest to continue working at Industry Dive – a fledgling B2B media startup – rather than attend Carnegie Mellon’s top-ranked Human Computer Interaction Master’s program back in 2013. Deciding whether or not to commit to CMU was a decision I wrestled with for a long time. I reached out to friends and family for advice, had a few restless nights, and even deferred acceptance for a year.
Looking back, I believe it was the open house weekend that made it so difficult to choose. The staff sold the program quite well. My mind was soon awash in dreams about what I might learn and whom I might meet.
At the same time, it was clear to me that my values and goals differed from many of my would-be classmates. I was not all that interested in a specialized UX (user-experience) career. Nor did I want to spend my time and effort within the walls of well-established corporations like Apple, Google, or IDEO. Because of these inclinations, I had serious concerns about taking on $80,000 in new loans to cover tuition and living expenses. It was obvious that the debt would lock me into a path that might not align well with my inner values. And the last thing I wanted to do at 24 was commit the next decade of my life to working in some corporate office to pay off loans. I also realized that taking on the debt would restrict my ability to undertake big risks – like starting a company – in pursuit of my long-term goals.
Having already tasted “startup” life for a few months, I craved the lessons taught by experience more than those found in the classroom. This same drive demanded I do battle with difficult problems that force you to think on your feet and constantly take risks. All of this flowed from a deep desire to carve out my own intellectual and professional path. I didn’t want to enter any funnel, however prestigious.
I wanted to take an uphill path. For as long as I can remember, it has been my intuition that constantly forcing yourself to perform highly diverse and difficult tasks while overcoming adversities is necessary to achieve the highest personal performance. Research conducted in the field of organizational psychology seems to support this hypothesis. In particular, when it comes to professional goals, “the more difficult the goal, the higher the performance achievement.” 
Finally, one Tuesday afternoon, I walked down to a liquor store near my office and bought a couple of packs of beers. I brought them back to a slightly confused team – I didn't drink at the time – and announced my intention to stay.
In most cases, it's not possible to say whether or not you made the "right" or "wrong" call on a career move. An alternate future is by its very nature unknowable. You just have to assess where you are at a given moment. There's no reason to look back and second guess or try to imagine what might have been. And, assessing this current moment, I feel that I am in a good place. My current work aligns with some of my core, inner values, and I'm often excited to head out to the office in the morning.
I'm reluctant to advise others on whether or not grad school is a good idea. Each person's situation is just so different.
Will a grad degree from a place like CMU help you land great tech jobs at startups and tech giants like Google, IDEO, Apple, et al.? Most likely. You'll also form lasting connections that will be useful in your industry career.
Can you land a job at those same companies without an advanced degree? Sure. People have done it. I did it at a media startup. It's just a different approach. If you are already a hacker with mad skills and you taught yourself how to build a compiler on a whim, you might not need an MS in CS. Also, some people, like myself, have an extreme desire to teach themselves, to learn independently. Caveat – I actually did go to grad school – LSE for Global Politics – before considering CMU. I'll write about that transition in a future post.
So, parting advice to people considering which road they should take...
Consider your personal values. Are you a highly-driven and independent person? Are those some of your core values? Are you driven enough to strike out and do your own networking? If your answers were yes, you'll probably be okay with or without grad school. Do you feel like you just don't have the time to learn what you need to know in your free-time outside your current job? Have you decided that you function best in highly-structured learning environments (I actually believe this is just conditioning that you can change)? Are you driven but unwilling to make your own industry connections? If your response was yes to those, maybe consider grad school.
Definitely analyze your financial situation. Seriously. If you think taking on $80K+ in loans is a good idea, you better make sure the program you're attending has a high placement rate in jobs paying in the mid to high six-figures. Even then, there are probably much cheaper alternatives with just as good ROI.
Finally, imagine that the level of your effort will determine if the earth continues to exist or is destroyed. Sure, this is dumb and sarcastic, but think about it... There are success cases in both camps. What do most of these people have in common? They gave it everything they had. They made their own luck. That's how you achieve career success. Nothing will be handed to you in this life. You have to earn it.
-  Deci, E. and Ryan, R. "The 'What' and 'Why' of Goal Pursuits: Human Needs and the Self-Determination of Behavior." Psychological Inquiry. Vol. 11, No. 4. 2000.
-  Locke, E.A. (2001). Motivation by goal setting. In Golembiewski, R.T. (Ed.), Handbook of organizational behavior (pp. 43-56). New York: Marcel Dekker, Inc.