Facing 65 Counts—Burglaries, Larcenies, Possession—He Committed To Sobriety

Derek Benson of Investing in Sobriety shares his journey from a highly structured childhood and elite athletics through pills, escalating addiction, crime, prison, and finally a sustainable recovery built on a mental-physical-spiritual blueprint and strong community.

Highlights:

* Early structure: military/boarding school; learned independence and discipline.

* First intoxication and growing access in high school; transfers to Avon Old Farms and The Hun School.

* Purdue years: injuries, pills in the locker room, and the slide from use → misuse → addiction.

* “Blind alley” spiral: funding use, losing work and relationships.

* Turning point: 12/12/2014—turned himself in; first exposure to AA in jail; later transferred to McDougall-Walker (high bond, no outside meetings).

* Letter that changed things: a family friend visits, connects him to 12-step support.

* Court offered Connecticut Valley Hospital (CVH) 42-day treatment; he took it, then faced a judge’s 10-year cap warning—fueling commitment to change.

* Recovery today: daily mental-physical-spiritual balance and a healthy circle of influence.

* Practical advice for the first 24 hours: reach out for help and stay open-minded.

* Derek’s project: Investing in Sobriety—conversations on personalized recovery blueprints.

More on Investing In Sobriety here: https://www.investinginsobriety.com/

Chapters

00:00 – Intro, gratitude for recovery community; Derek at ~10 years sober.


03:20 – Childhood & military/boarding school; structure and early independence.


06:25 – First drunk; access increases; transfer to Avon Old Farms.


08:00 – Senior year path to The Hun School; athletic exposure.

10:32 – Purdue: pills after injuries; shift toward addiction.


12:53 – Use vs. misuse vs. addiction; trouble at college party.


28:21 – “Blind alley” metaphor; life narrows around using.


30:06 – Losing work, unhealthy circles, doing anything for money.


31:41 – Criminal activity escalates; path to prison.


33:38 – 12/12/2014: turns himself in (beginning of recovery).


41:04 – First AA in Hartford Correctional.


42:17 – Transfer to McDougall-Walker; no outside meetings; pivotal letter to family friend.


45:47 – 65 pending charges; attorney lays out CVH option.


47:01 – CVH 42-day program; willingness and early momentum.


49:27 – Judge’s 10-year cap warning; why he doubled down on change.


52:48 – Derek’s recovery blueprint (mental-physical-spiritual).


55:55 – Building a healthy circle of influence.
57:37 – Advice for day one: reach out & be open-minded.


58:39 – Derek’s podcast: Investing in Sobriety.

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