Christian OsgoodCEO, Multifamily Strategy · CEO at Multifamily Strategy

Past Success Doesn't Guarantee Future Results

12 Jun 2026 · 1 min

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0:45

In this brief YouTube monologue, Christian Osgood shares his personal experience of quitting an outside sales job during the 2020 Washington State lockdown. He admits that leaving too early was stressful and not the best decision, emphasizing that past success does not guarantee future outcomes. Osgood advises listeners to stay in their current job for roughly 2.5–3.5 years (often framed as a 3–5 year window) to allow a side business to prove its viability and potentially outperform the job before making a full‑time switch.

Chapters

I am one who left too early, so I cannot coach that from, uh, practical experience. 2020 hit, I was an outside sales rep. You couldn't go outside in Washington State for 2 years. I was like, screw it, I'm out. Just because it worked for me does not mean that it's a good idea. Past success does not dictate future results. You will not, uh, it, it was not the best idea. It was more stressful. Uh, just because it worked doesn't mean it was the best way to do it. And certainly If you can keep a job and continue to succeed there, give it 2, again, 2.5 to 3.5 years. That, for most people, is that 3 to 5 year window is where you really get the legs under your business where you're like, hey, this is outperforming my job. If you're not there yet, stick it out. Yeah. And that's the switching mechanism, right? This is outperforming my job.