Infinite Careers is a collaboration between Career Services (CAPD) and the MIT Alumni Association to explore career paths and the non-linearity of career decision making. Read profiles of alumni with unique career paths, hear their stories and network at a series of talks.

Education

  • MIT – Bachelor Of Science, Mathematics
  • Harvard – Masters in Computer Science

Bio

Win Treese is an adjunct Lecturer in Computer Science at Brandeis University and a principal with Serissa Research, an independent consulting firm. At Brandeis, he teaches Introduction to Computer Security. His consulting work most recently has focused on analyzing software source code involved in litigation.

Win began his career working on staff at MIT’s Project Athena. From there, he moved to Digital Equipment Corporation’s Cambridge Research Laboratory when it opened, and later joined the founding team at Open Market, one of the first companies building software for Internet commerce. He led the software development team at supercomputer startup SiCortex and served as Director of Projects and Programs for a time at Boston University’s Hariri Institute for Computing and Computational Science and Engineering.

From 1998-2010, Win wrote a regular column for Networker magazine, published by the Association for Computing Machinery. He is co-author of the book “Designing Systems for Internet Commerce” with Larry Stewart (EE ’76) and a recent collection of poetry, “In the Cloud: Poems for a Technological Age”. He chaired the working group of the Internet Engineering Task Force that standardized Transport Layer Security from its inception through the publication of the draft standard. He is an inventor with 13 patents and was named a “High-Tech All Star” by Mass High Tech in 1999. Win also served as a member of the advisory board for the New England Center for Investigative Reporting and is an elected trustee of his town’s public library, where he also helped start and lead a Girls Who Code club. He is currently at work on his next book.

What has been the most rewarding aspect of your career?

I’ve been very lucky in getting to work with smart, interesting people and doing interesting things together. That’s been much more important to me than the financial particulars, although those often go together.

What motivates you to do the work that you do?

Doing what I find interesting, and where I’m learning something. More than once I have pursued something I was simply curious about (or mildly obsessed with, for whatever reason), and it later paid off in unexpected ways. If I don’t find the work interesting in some way, I find it very difficult to carry it out. There’s a trick here, of course: if it doesn’t seem interesting, how can I find a different angle that is?

Making decisions, especially important-feeling career decisions, is really challenging for people at all stages of their career. What strategies have you used to make career decisions? 

One of my favorite strategies is to flip a coin. What matters, however, isn’t the result from the coin—it’s how you feel about the result. If your gut reaction to the coin is “ugh”, don’t do that! Aside from that, I look at the challenge, the problems to be solved, and the people. I want to have a clear idea of why I am going down that path. The times I didn’t have a clear “why” were the times I didn’t succeed. I’ve been fortunate in that, during the time I have worked in computing, the downside risk has been minimal, and there have always been new things to do. Not every choice in a career is like that.

What professional development experiences or opportunities shaped your early career?

A few months into my first real job, working on Project Athena at MIT, I was sent to represent Athena at a computing workshop at Berkeley. The workshop only had about fifty people there, and I was representing MIT, so it was easy to join in conversations, even with very experienced and knowledgeable experts. A few months later, I went to a much larger conference, where I was able to hang out with the well-known people I had met at the workshop—and meet many more people. I was also giving presentations, which made it easier to talk to people because many of them would start a conversation. I had no strategic plan for this, but the connections I made early on have been very valuable over the years, on both professional and personal levels. The result is that every job I’ve had has come about from a connection or introduction.

What’s the best piece of career advice you’ve received?

While I was working for Project Athena, I took a couple of classes as an MIT employee. It’s a fantastic benefit, of course. I had gotten interested in technology and policy, so when I started thinking about what’s next after Athena, I considered graduate school in that area or going to law school as a path into it. Around that time, I was introduced to the founding director of Digital Equipment Corporation’s new research laboratory in Cambridge. We met for lunch, and I talked openly about what I was thinking about. His advice was, more or less “if there’s something other people find hard, and you find easy, DO THAT.” Reflecting on that, I realized that, for whatever reason, I found software easy, and certainly most people didn’t. Instead of going back to school then, I ended up going to work for him, which paved the way for many other things that happened. It’s another time I felt lucky both to have gotten the advice and to have had enough clarity on my own about how to answer the question.

What career advice do you have for current MIT students, or those interested in entering your industry?

Technical skills are table stakes. You’ve been at MIT; you almost certainly have them. Figure out what else you bring to the table that’s interesting. When looking for a job, think about “what problem do they have?” and “how can I help them solve it?” Keep in mind that they may not know what problem they need to solve. In the bigger picture, think about the life you want, not just the career or the job. Where do you want to live? Who do you want to have around you? What rhythms of work do you want? Then work toward your personal vision. Always be on the lookout for how you can make a contribution to help a team and organization accomplish its goals. As you gain experience doing this, you will also gain autonomy in choosing where to focus. Work on your communication skills, both speaking and writing. Communicating well—especially about technical topics to less-technical audiences—is a powerful career booster. While you’re at it, use writing as a way to clarify your thinking. If you haven’t discovered this, it really works!

Do you have any tips for networking or job searching for current students and recent graduates?

Meet people in person. Get involved in projects and activities—not necessarily technical—that bring you in contact with other people. Get to know them, help them, and it will come back to you in surprising ways. If you’re interested in software, start answering questions and fixing a few bugs on an open source project. In other areas, find other ways to connect and contribute to what others are doing. Volunteer with organizations doing things you think are important. Make it possible for opportunities to find you.

Last edited: September 2024