Tacking Against the Wind: On Needing a Mentor in My Career

Thirty years since graduating college, after spending a decade in software development and another 20 years in database administration and engineering, I find myself at a crossroads. The migration of the application I support to a SaaS successor will affect me in the coming year and I dread losing use of the tradecraft that’s been the keystone of my career. My challenge is to plot the best course forward, and I’m seeking a navigator in the form of a mentor to guide me to what may be the start of the finale of my career.

The Marina at my Dad’s island of Zlarin, Croatia. (August 2018)

To review my career for the past 30 years, it helps to imagine you’re sailing a sailboat. You have a destination on the map and your partner is the wind, which is vital but won’t always cooperate with you. You plot your course, note how the wind shifts as you keep the boat in trim for speed and balance, and change tack if you find yourself having to sail upwind, like going up switchbacks on a mountain.

My career has been like a boat race, each course leg running about 4 years in the form of a new job. With each job, I learned and applied new skills until the wind shifted, whether to try a different challenge, move up the pay scale or avoid career stagnation. It was working relatively well, starting off with desktop development and learning the basics of data modeling, later learning Oracle and SQL Server as an accidental DBA, followed by data warehousing and being an enterprise DBA.

That enterprise DBA leg was transformative for me in many ways. In a span of 11 years, working with SQL Server became a vocation. My topics of knowledge to learn mushroomed overnight, including how to use SAN storage, high availability with clusters, and administering over 100 servers with SMO scripting. Going to my first PASS Summit exposed me to our great SQL Server community and on a track of not only learning, but also sharing. At my peak, I was attending my local user group in NJ, SQL Saturdays in the Northeast, answering questions on Stack Exchange and posting tech solutions on my blog. I had wind in my sails and I was enjoying the ride.

Sailboat Near Alcatraz (August 2021)

Until I ran aground. A little less than 5 years ago, I opted to try my hand at a SSIS ETL job very close to home, but in a setting that I wasn’t ready for. I learned the hard way that technical knowledge of a platform or two isn’t enough. Knowledge of your employer’s products and services, current development techniques and the industry’s culture all need to come together in the most demanding of environments. Sometimes it takes training, sometimes it takes time, and sometimes it takes luck. It was the first time I ever left a job less than 4 months in. I am grateful to have had a place to return to, but it left me wondering how close I was to sinking.

I’m nearly 5 years into my latest leg in my journey with SQL Server, but I don’t have the DBA hat on. My role is that of the engineer and analyst, focusing on T-SQL, SSIS and ETL design to supplement a timekeeping application’s ETL system. I miss wearing the DBA hat though, especially everything in Azure my current role doesn’t require, so I’ve been trying to keep my passion in sight. First, I renewed my MCP certifications, both as a developer and DBA. Then, with guidance from an MVP, I’ve built a home lab to try out AGs and anything my work doesn’t require me to do. As time permits, I make good use of PluralSight and DataCamp to keep studying, dabbling with Python, PowerShell, Databricks and more.

Sunset at Zlarin, Croatia (August 2018).

My challenge today is finding my best point of sail while navigating around multiple shoals of middle age. On the home front, I cherish my time helping my son adapt to high school while trying to figure out with my wife how to renovate our aging home. Before morning coffee ever kicks in, I strive to maintain my late parents’ legacy by learning Croatian with a tutor six time zones away, but with scant energy for homework. At work, it’s a battle to keep up with the near-constant stream of tasks I track on Trello while noting on the horizon the SaaS solution is coming. I can make time to train, but what track would fit me best, and to what end?

Should I embrace what is SaaS and let what I know of SQL Server start to fade? Should I rally and find a niche for it like I have for the last 5 years? Maybe I should setup an LLC and seek a side hustle as a fractional DBA? Is a lateral move within my organization in the cards, or may I have to cast off and find another shore?

I’m coming up to the top of the mark of the course that is the regatta race of my career. This is where I raise the spinnaker to catch the wind. What course should I plot and will you be my navigator to guide me?