u/triplegemBDS

I'm 56, currently a teacher with 26 years service. I'm planning to leave my job in June 2027 and move to Latin America. I'm currently developing a freelance, remote career. Looking for feedback on whether my plan is sound.

Current situation:

• Teaching salary: $120K
• Freelance income (first year): $25K YTD, expecting $50K+ annualized
• Total assets: ~$713K (403b: $460K, Roth: $67K, HSA: $18K, Cash: $170K)
• Debt: $0
• Expenses: $3,150/month in US, expecting ~$3K/month abroad

The plan:

Phase 1 (Sept 2026 - June 2027): Final teaching year. Max out all retirement accounts (403b, Roth, HSA). Cash savings goal = $200k

Phase 2 (July 2027 - Oct 2029, "the gap"): Leave teaching, move abroad, work full-time freelancing. Live on freelance income (presumed at least ~$50K/year pre-tax), expenses ~$36K-$40K/year. Don't touch retirement accounts or cash unless emergency.

Phase 3 (Oct 2029+): Pension kicks in ($58K/year guaranteed, COLA protected). Continue freelancing, invest surplus money in retirement accounts.
Age 70 = start retirement withdrawal. Start social security payments (~500/month)

*Destination country does not tax foreign income
*Health insurance is included in my 36k-40k estimate ($750/month)

The freelance career: Just started but getting contracts (Upwork) and am working as much as I can with a full time job. I was just offered a full time job at 150k which helped to validate the path.

I could stay teaching for another year (total 2 more). I would again, max all retirement accounts and my pension would bump up to $63K per year.

I could keep doing that but clock keeps ticking and I want to enjoy another dream.

I don't have kids. Not married.

My questions:

1. I have a 22-month gap without pension. I'm relying on a website (Upwork) for my livelihood over a US State job with the most security one could hope for. Is this nuts?
2. Should I be doing Roth conversions during the gap years (lower income bracket)?
3. Any major blind spots in this plan?
4. Is my asset allocation appropriate (84-91% stocks, 14-year runway until pension)?

If you see a hole, please call it out! Looking for any feedback. This is my first time posting (on Reddit!) and will say thank you in advance!

I'm 56, currently a teacher with 26 years service. I'm planning to leave my job in June 2027 and move to Latin America. I'm currently developing a freelance, remote career. Looking for feedback on whether my plan is sound.

Current situation:

• Teaching salary: $120K
• Freelance income (first year): $25K YTD, expecting $50K+ annualized
• Total assets: ~$713K (403b: $460K, Roth: $67K, HSA: $18K, Cash: $170K)
• Debt: $0
• Expenses: $3,150/month in US, expecting ~$3K/month abroad

The plan:

Phase 1 (Sept 2026 - June 2027): Final teaching year. Max out all retirement accounts (403b, Roth, HSA). Cash savings goal = $200k

Phase 2 (July 2027 - Oct 2029, "the gap"): Leave teaching, move abroad, work full-time freelancing. Live on freelance income (presumed at least ~$50K/year pre-tax), expenses ~$36K-$40K/year. Don't touch retirement accounts or cash unless emergency.

Phase 3 (Oct 2029+): Pension kicks in ($58K/year guaranteed, COLA protected). Continue freelancing, invest surplus money in retirement accounts.
Age 70 = start retirement withdrawal. Start social security payments (~500/month)

*Destination country does not tax foreign income
*Health insurance is included in my 36k-40k estimate ($750/month)

The freelance career: Just started but getting contracts (Upwork) and am working as much as I can with a full time job. I was just offered a full time job at 150k which helped to validate the path.

I could stay teaching for another year (total 2 more). I would again, max all retirement accounts and my pension would bump up to $63K per year.

I could keep doing that but clock keeps ticking and I want to enjoy another dream.

I don't have kids. Not married.

My questions:

1. I have a 22-month gap without pension. I'm relying on a website (Upwork) for my livelihood over a US State job with the most security one could hope for. Is this nuts?
2. Should I be doing Roth conversions during the gap years (lower income bracket)?
3. Any major blind spots in this plan?
4. Is my asset allocation appropriate (84-91% stocks, 14-year runway until pension)?

If you see a hole, please call it out! Looking for any feedback. This is my first time posting (on Reddit!) and will say thank you in advance!

I'm 56, currently a teacher with 26 years service. I'm planning to leave my job in June 2027 and move to Latin America. I'm currently developing a freelance, remote career. Looking for feedback on whether my plan is sound.

Current situation:

• Teaching salary: $120K
• Freelance income (first year): $25K YTD, expecting $50K+ annualized
• Total assets: ~$713K (403b: $460K, Roth: $67K, HSA: $18K, Cash: $170K)
• Debt: $0
• Expenses: $3,150/month in US, expecting ~$3K/month abroad

The plan:

Phase 1 (Sept 2026 - June 2027): Final teaching year. Max out all retirement accounts (403b, Roth, HSA). Cash savings goal = $200k

Phase 2 (July 2027 - Oct 2029, "the gap"): Leave teaching, move abroad, work full-time freelancing. Live on freelance income (presumed at least ~$50K/year pre-tax), expenses ~$36K-$40K/year. Don't touch retirement accounts or cash unless emergency.

Phase 3 (Oct 2029+): Pension kicks in ($58K/year guaranteed, COLA protected). Continue freelancing, invest surplus money in retirement accounts.
Age 70 = start retirement withdrawal. Start social security payments (~500/month)

*Destination country does not tax foreign income
*Health insurance is included in my 36k-40k estimate ($750/month)

The freelance career: Just started but getting contracts (Upwork) and am working as much as I can with a full time job. I was just offered a full time job at 150k which helped to validate the path.

I could stay teaching for another year (total 2 more). I would again, max all retirement accounts and my pension would bump up to $63K per year.

I could keep doing that but clock keeps ticking and I want to enjoy another dream.

I don't have kids. Not married.

My questions:

1. I have a 22-month gap without pension. I'm relying on a website (Upwork) for my livelihood over a US State job with the most security one could hope for. Is this nuts?
2. Should I be doing Roth conversions during the gap years (lower income bracket)?
3. Any major blind spots in this plan?
4. Is my asset allocation appropriate (84-91% stocks, 14-year runway until pension)?

If you see a hole, please call it out! Looking for any feedback. This is my first time posting (on Reddit!) and will say thank you in advance!