I played 3 sanctioned events in 2002 with some fluky results, so I won't include that. I started again in 2010. My milestones are as such:

3/25/10: ZEN/ZEN/WWK Draft
Milestone: First Sanctioned event since 2002
Record / Placement: 1-3 (18/23)

4/24/10: ROE Launch (Sealed)
Milestone: First time > 50% Record / Placement: 3-1 (5/36)

8/21/10: GPT (M11 Sealed) Milestone: First REL-Competitive
Record / Placement: 4-2 (11/36)

10/28/10: SOMx3 Draft
Milestone: First undefeated / First 4-0 Start
Record / Placement: 4-0 (1/37)

11/6/10: PTQ Scars of Mirrodin (Sealed)
Milestone: First PTQ
Record / Placement: 4-2 (45/161)

10/15/11: States (Standard)
Milestone: First Constructed REL-Competitive
Record / Placement: 3-2-4 (lol) (99/278)

10/15/11: PTQ Gatecrash (Sealed)
Milestone: First 5-0 Start
Record / Placement: 6-3 (26/320)

8/9/14: GP Portland (Team Sealed)
Milestone: First GP
Record / Placement: 5-4 (151/649)

11/16/14: PTQ Fate Regorged (Sealed)
Milestone: First Top 8! Record / Placement: 7-2-1 (4/180)

11/16/14: PTQ Fate Regorged (Sealed)
Milestone: First Top 8! Record / Placement: 7-2-1 (4/180)

6/7/15: PPTQ 2016 (MM2 Sealed)
Milestone: First REL-Comp Win! Record / Placement: 7-0-2 (1/55)

I think I'm progressing, although I recognize how long it has taken to get to this point. In my defense, I took a lot of time off during Theros because I was unemployed and hated that block and also I only recently got really into competitive events due to the PPTQ system. In the past, I'd really only hit the occasional 1-2 PTQs a year and I'd treat a random GP trial like an FNM if I was up for playing magic that day. I can't say where there were any lightbulb moments. Some days I feel like the greatest player ever and like I could win on any given day against any given opponent. Other days I feel like a total scrub that not be so invested in a children's game and should get better hobbies. Goes to show the variance of magic sometimes.