Life & fun · alternatives · 2026

24 alternatives to Nomadic Entrepreneurs: Sean D’Souza on Why a Three-Month Vacation Every Year is Not Impossible

Sean is known for his commitment to 3 month vacations.

Below are 24 products that do a similar job, ranked by how close each is in meaning and then by launch-day votes. Nomadic Entrepreneurs: Sean D’Souza on Why a Three-Month Vacation Every Year is Not Impossible launched in 2016; newer entries below may have overtaken it.

1
Destinations by Remote Year▲107
Take your job on a month-long work & travel experience 💻
2020 · remoteyear.com · its alternatives →
2
YonderWork▲127
Two month getaways for remote workers ✈️🌴
2016 · yonderwork.com · its alternatives →
3
Remote Year▲285
Keep your job, see the world, leave the planning to us 🏝️
2014 · remoteyear.com · its alternatives →
4
Remote Year: Four-Month Experience▲93
Work and explore the world with a vibrant global community
2017 · remoteyear.com · its alternatives →
5
21 Days Challenge▲96
A set of challenges to be accomplished every day for 21 days
2019 · play.google.com · its alternatives →
6
Off The Grid▲101
Join 30 inspiring people for 10 days of phone-free travel.
2018 · its alternatives →
7
Nomad Haven▲107
Save up to 22% of your annual salary as a digital nomad
2023 · its alternatives →
8
Bootstrapped - 58: Vacations▲57
Ian and Andrey discuss vacations, unlimited licensing & more
2015 · bootstrapped.fm · its alternatives →
9
Founder's Journey - How we’re fixing “unlimited” vacation▲60
We’re fixing “unlimited” vacation + public time-off board
2016 · baremetrics.com · its alternatives →
10
Trameter▲235
Create a customized vacation plan
2024 · apps.apple.com · its alternatives →
11
Law of 100▲194
Make or break a habit in 100 days.
2022 · its alternatives →
12
No Questions Asked▲96
Get one new experience per week, for 6 weeks
2017 · its alternatives →
13
80 Days ▲67
Choose your own route around a 3D globe
2015 · inklestudios.com · its alternatives →
14
How Many Days ?▲53
Because Everyday Matters.
2017 · howmanydays.xyz · its alternatives →
15
30 Days of Fun▲82
Challenge yourself to do something fun every day for 30 days
2021 · its alternatives →
16
Terminal 3▲5
Spend one month in a different destination for six months
2015 · its alternatives →
17
Unstagnate #6 - Connor Grooms: Achieving Epic Results in 30 Day Challenges▲56
30-day Strategies from a guy who learned Spanish in a month
2016 · traffic.libsyn.com · its alternatives →
18
Remote Year - Singles Edition (1 month)▲22
Travel and work remotely for one month with other Singles
2024 · remoteyear.com · its alternatives →
19
Social Media Calendar Special Days▲127
List of all special days and weeks in the world
2022 · ugurkilci.com · its alternatives →
20
Nomad Proof▲163
Generate unlimited onward travel plans in 10 seconds
2017 · akuwin138slot.com · its alternatives →
21
TwentyOne▲108
Build habits in manageable bites, together
2023 · apps.apple.com · its alternatives →
22
Time and Again▲83
Easily keep track of "once in a while" tasks
2021 · apps.apple.com · its alternatives →
23
As Told By Nomads - Evo Terra and Shiela Dee▲70
Opportunistic Travel and the Digital Nomad Lifestyle
2015 · uydmedia.com · its alternatives →
24
21 Days Community▲16
Forge Unbreakable Discipline. 21 Days. Zero Compromise.
2025 · 21days.community · its alternatives →

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Ranked by how close each launch is in meaning, then by votes. Prices were read from each product’s own site when checked and can change. Refine with your own description →