Then → Now · 2026
The encouragement holds up, but in 2026 the first question is arguably whether AI is eating your chosen skill.
What it said (2018) ↓
The timing never feels right. Imagine the status quo for 40 years, make a hypothetical plan, and cost it with the Dreamline worksheet from The 4-Hour Workweek.
Check Upwork for side projects that match your skills; "there are always other options" (link to a Weebly blog).
What happened (2026) ↓
The Dreamline/lifestyle-costing link now redirects to tim.blog/lifestyle-costing/ and still works. The Weebly "other options" link is dead (404). (link check 2026-09-30) tim.blog
Upwork is still the default marketplace but has repriced. Since May 2025 freelancers pay a variable 0–15% fee instead of a flat 10%. Upwork Help
Verdict · Held up: 5 / 10 · Full 2026 update
- The timing to go freelance never feels right, so you should make a plan and cost it now.Still valid evergreen
- Aspiring freelancers should have faith in themselves and simply make the jump.Partly outdated for AI-exposed skills
Original post · 5 January 2018
Is This It?
One way to make yourself more comfortable with considering the alternatives, is by imaging what life would be if it would stay like this for the next 30-40 years or so. ‘No, the office job isn’t that bad, I can stick around a little while longer…’ But imagine having to go there each and every day for the next 40 years. Yes, your apartment is just fine, but do you really want to stay in that boring city where never anything happens and it’s always raining? Of course you can deal with that annoying, time-consuming and soul-crushing client through one more sale, but what if you have to do that for as long as you’ll work? Maybe you should indeed reconsider the alternatives, because the time will never seem right.Make A Plan
No, of course you’re not actually going to make the move, but just write down your hypothetical plan. What would be the minimum you would need? Break down all the needs (both financial and action points) into small chunks. Which exact stept would you need to take? How much money would each step require? If you don’t know how to write it down, then use the worksheet of the Dreamline from ‘The 4 Hour Workweek’. The other way around might be necessary, too. How much money would you need in order to move to New York? Now where are you going to get that money from? Maybe you can find a few extra clients. Maybe you can do some small, extra job from home. Have a look at Upwork to have an idea of which projects would match your skills. Just remember, there are always other options to get somewhere. And all of a sudden, that hypothetical plan is not so hypothetical anymore…Have Faith In Yourself
The main, underlying reason why we choose not to do something, if often because we don’t have any trust in our own skills and knowledge. It’s such a shame, and so unnecessary! Think about someone who is an example to you, someone who took the risk and just did it. Believe me, he or she does not possess any superhuman powers, other than just having guts. So why wouldn’t you be able to do it? If he can do it, you can do it.The Time Is Definitely Now
The time never seems to be right, neither when you want to have a baby. However, for some reason ‘we really want one, so we will just make it work’ is totally acceptable for most people. And that’s it. If you truly want something, thought it through and know which steps to take, you will just make it work.What happened after this was written
Claims then:
- The timing never feels right. Imagine the status quo for 40 years, make a hypothetical plan, and cost it with the Dreamline worksheet from The 4-Hour Workweek.
- Check Upwork for side projects that match your skills; "there are always other options" (link to a Weebly blog).
- Have faith in yourself.
What happened since:
- The Dreamline/lifestyle-costing link now redirects to tim.blog/lifestyle-costing/ and still works. The Weebly "other options" link is dead (404). (link check 2026-09-30) tim.blog
- Upwork is still the default marketplace but has repriced. Since May 2025 freelancers pay a variable 0–15% fee instead of a flat 10%. Upwork Help
- Starting as a freelancer appears riskier in AI-exposed categories such as writing, at least in the short run (the cited study covers writing and image work, not translation). WashU Olin
Named tools/orgs status:
| Name | Then | Now | Evidence |
|---|---|---|---|
| 4HWW Dreamline worksheet | Linked | Live, redirected to tim.blog | link check 2026-09-30 |
| Upwork | Side-project source | Active; variable 0–15% fee since 2025-05-01 | Upwork |
| Weebly "other options" post | Linked | 404 | link check 2026-09-30 |
Verdict: Motivational: Still valid (evergreen). Its "just jump" framing is Partly outdated for AI-exposed skills.
Headline finding: The encouragement holds up, but in 2026 the first question is arguably whether AI is eating your chosen skill.
Re-verified 3 November 2026: 2 claims confirmed, 0 corrected, 2 hedged, 0 removed.
Researched 30 September 2026 and re-verified against the sources on 3 November 2026. Sources are linked in each point. Items marked "unverified" could not be established and are not guessed.
