Brett Trainor Unplugged

15 Ways I've Made Money Since Leaving Corporate

August 1
31 mins

Episode Description

Making money outside corporate is easier than landing your next corporate job. After a thousand-plus conversations with people leaving corporate, the blocker is almost never skill or experience. It's that we overcomplicate it.

This one is all mechanics. If you're 45+ and trying to make your first dollar outside corporate, or just want to stop betting everything on one paycheck, this is the playbook.

In this episode:

  • Your real number: why you think in cash flow now, not salary, and why it's lower than you'd guess

  • Why one boss is the riskiest bet you can make

  • Separating mission from money so you fund the life without burning out

  • 15 ways I've actually made money since leaving corporate, from higher-effort work to low-friction income anyone can start

  • Three live examples with real numbers: the guy negotiating car deals, a wedding-dress business I built in 4 hours for $10, and the Amazon Influencer Program

  • A simple four-part filter to score any idea: pay, demand, ease, repeatability

Watch the version with slides on YouTube, or grab the deck from the resources below.

Money is solvable. Time is the thing you can't get back. Stop trading so much of it.

THE 15 WAYS (quick reference)

Higher-effort income (monetize your corporate experience — great cornerstone accounts, but more hours):

  1. Fractional leadership

  2. Consulting (project-based)

  3. Solo consulting

  4. Advisory

  5. Business development (setting meetings for brands in your network)

  6. Reselling services for smaller brands

  7. Affiliate sales

Audience-based (helps to have a following): 8. Sponsored posts 9. Paid community 10. Speaking 11. Paid content / brand sponsorships

Low-friction income (anyone can start, small audience or none): 12. Paid workshops 13. Coaching (business, career, or a hobby — you just have to be a step ahead) 14. Facilitating webinars 15. User-generated content (UGC)

Bonus area to dig into: AI services for business owners.

THE FILTER (score each idea 1–10)

  • Pay — how much per hour?

  • Demand — is this a need-to-solve problem, not a nice-to-solve one?

  • Ease — how fast and simple to deliver?

  • Repeatability — can you do it again and again?

LINKS & RESOURCES

Watch this episode with the slides on YouTube → https://youtu.be/p5rxv-f1M7k

Download the deck (the 15 ways + the filter) → https://stan.store/thecorporateescapee

Free: The Time Rich Starter Kit (six worksheets to see where your time actually goes) → https://stan.store/thecorporateescapee/p/see-where-your-time-actually-goes

The Time Rich Collective (connect with Gen Xers on the same path) → [COMMUNITY LINK — drop in]

Website → https://timerichproject.life

Mentioned in this episode:

CHAPTERS / TIMESTAMPS

00:00 — Making money outside corporate at 45+ 01:00 — The real blocker: we overcomplicate it 02:20 — The five things this episode covers 02:50 — 1. Stop thinking salary, start thinking cash flow 04:00 — No pension, and becoming a high-functioning lazy person 05:00 — 2. Why one boss is the riskiest bet 06:45 — 3. Separate mission from money (thanks, Diana Alt) 07:50 — 4. The 15 ways I've made money (deck on YouTube) 08:30 — What low-friction income actually means 09:00 — Higher-effort: fractional, consulting, advisory, reselling 11:20 — For the record: I've spent $0 on marketing 11:40 — Audience-based: sponsored posts, community, speaking 12:20 — Low-friction anyone can start: workshops and coaching 15:00 — UGC: my favorite way to start 15:40 — The solo-business boom (WSJ) 16:10 — Solve one simple problem, not all of them 16:40 — AI services for business owners 18:30 — Example 1: Tommy negotiates car deals 20:30 — Example 2: the wedding-dress business I built in 4 hours 24:30 — Example 3: the Amazon Influencer Program 26:30 — The filter: pay, demand, ease, repeatability 27:50 — Don't chase shiny objects 28:40 — Money is solvable

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