From probation officer to entrepreneur

5 tips I took out of the county jail into business

5 min readJan 27, 2014


In my early twenties, most social encounters began like this:

“Whoa, a probation officer?”


“Can you arrest me?” [nervous laughter]

I might’ve been the youngest probation officer the country has ever seen, but no, I was not responsible for arresting people. I supervised folks after they had been arrested. Sure, I issued a few warrants, but as a probation officer, I was responsible for supervising individuals within the community, ensuring they posed no harm to their surroundings or to themselves.

What began as a volunteer requirement for an undergraduate psychology course evolved into a paid position writing recommendations for judges. I would spend hours interviewing DUIs and DWAIs, people who got caught drinking and/or drugging and driving. I’d then research state and nationwide government databases (yes, these exist) for criminal backgrounds. Had he been in trouble before or was this a fluke occurrence? Was she “amenable to treatment” or destined for a repeat offense? I heard every story: the overworked university professor with a coke problem, the clinically depressed artist who just moved from NYC and didn’t know how to get around without the subway, the stay-at-home mom who had one too many at dinner and got pulled over for a missing taillight.

After the judge decided upon their requirements, I’d see many of them again, tracking “minimal to medium risks” to make sure they did everything that was ordered — go to alcohol classes, seek treatment, stay out of trouble. The caseload was upwards of 300 individuals, a large metal cabinet sitting in the corner holding unique case numbers and names.

Eventually I was promoted and handed a binder filled with detailed contact sheets of “medium to high-risk” teenagers. I memorized their names, their schools, their parents (if they had them), and how frequently I needed to see them. Each kid required varying levels of supervision, ranging from a phone call every few months to daily check-ins. I became a therapist for families, liaison for therapists, and sounding board for government officials.

I look back on this now, and it seems like a different life.

I’m often asked how I made the transition from probation officer to entrepreneur. In hindsight, they’re not all that different. Carrying a badge prepared me for business in ways I never could have imagined.

Look for the good

The “delinquent” isn’t going to school, but her notebook is filled with scribbles and drawings. The sketches are of dead birds and crying women, but there’s evident skill behind them.

“If you can make it to school two weeks straight, I’ll take you to the paint-your-own-pottery-studio,” I offered. It worked. Before I knew it, the girl who came with warnings from colleagues (“Good luck with this one.”) was now a model student.

Most any individual I worked with — someone on their first DUI or a vandal who broke into a pharmacy and was found in possession of Control I substances — appreciated the fact I treated them with respect.

Whether colleague, client, or employee, you’ll get a drastically different performance from someone who believes you respect them and value them as a human being, in spite of their mistakes and flaws. Give someone responsibility, and they’ll feel a sense of ownership and pride. It might take some searching to find someone’s true talents, but if you’re willing to look, they’re there.

Frame the situation

People on probation are sent away from court with a laundry list of things they must do (and not do). This typically includes the basics: staying clean, curfew hours, don’t get in trouble — but it can also include paying fines, going to therapy, even maintaining employment.

I would ask my clients for recommendations of their own, reminding them that since they are “in the system,” there are all sorts of government programs at their fingertips. Don’t have a high school diploma? Let’s find a GED program. Struggling to keep a job? Let’s enroll in a job-readiness program. I even started an after-school program for juveniles, convincing a slew of community artists and musicians to share their art for free (I took loved watching these kids learn Walt Whitman and hip hop routines).

If you’re in a situation that doesn’t seem to be giving you the results you want, see how you might redefine the problem or adjust the environment in a way that positions the outcome you’re looking for. You may need to ask a colleague for her input or work on understanding the situation from your client’s point of view.

Ask the right questions

“Are you an alcoholic?”


“How many nights a week do you drink?”


I learned quickly that in a world of felons and misdemeanors, asking the right questions was instrumental to my success.

In grad school, I learned there’s an actual term for asking questions in a way that points out the discrepancy between someone’s word and action: it’s called motivational interviewing (i.e., woman wants to get off probation but keeps testing positive for methamphetamines; man says he wants to find a job but hasn’t gotten off his couch in a week). Knowing what questions to ask and how to ask them is one of those skills that can propel you forward in any industry.

The ability to ask good questions is largely correlated to being well-informed. Listen to any quality journalist, and you can tell they’ve done research on the subject before the interview (Guy has mastered this).

Before you head into a meeting or meet with a client, do some footwork. Your question can demonstrate you have a larger strategy in mind or you’re looking to gain additional information to add to your existing knowledge base. Ask questions in a way that shows you’ve done your reading on the subject.

Go in with a team

House visits are an instrumental part of community supervision. But you never go alone. County dollars are spent on training in which government officials learn how to safely navigate environments in teams. One officer is labeled “Contact,” and their primary mission is to speak with the client and make sure they’re following court orders. “The Watch” is to observe the surrounding area and look for signs of looming danger.

Same goes for entrepreneurs and business folk. If you don’t have a good partner keeping an eye on impeding obstacles, you’re screwed. It’s too easy to get focused on one thing and lose sight of the big picture.

Know your shit

I had to go head to head with public defenders, stand in front of some pretty intimidating judges, and tell panels of assorted community workers that their ragtag approach to treatment wasn’t cutting it. In these kinds of situations, I couldn’t afford to pause or be seen as if I was questioning my own reasoning. If I was doubtful or scared, I sure as hell couldn’t show it.

Whether pitching a business idea or presenting your point of view, you need to be able string together a sound argument with logical statements to support it.

Most entrepreneurs don’t know exactly what they are doing, but they’re so good at convincing their audience that they do, they land the client/job/grant/proposal/funding. Confidence goes a long way, no matter where you are.




After co-founding Learning House, an education center in Nepal, I coach and create. You may see my writing on the internet.