You must pick a point in human history before the 1950s to be spend the rest of your life in. What era and place would you choose?
You would still have the same age, gender, personality, skin color, etc. and you would be able to speak at least one local language and would know basic information of the era and place. Your family, social standing, and such would be randomly picked.
I mean, tune it just right and you can get the Industrial Revolution started a couple millenia early and maybe bypass the whole colonialism nonsense. Middle ages is too late, too much theocracy. Common knowledge gets you in grecorroman spaces, but maybe you can overshoot a touch and get some nice Phoenician traders to bankroll your plan to mass produce bycicles or Ikea-style furniture and ship it all over the Mediterranean.
Just... hope you stay healthy or that the rules let you pack a bunch of antibiotics. Or maybe learn a bunch of modern medicine before you go. Maybe prioritize the whole "discovering penicillin" thing when you get there.
Not necessarily insurmountable, but still a good point.
You may still have an easier time getting things up and running as a slave in antiquity than as a serf in the Middle Ages, depending on where you end up. Pretty sure you'd have a better shot as a slave in antiquity than in the US or other colonial areas, both because colonialism reeeeally sucked and because you'd have relatively more valuable skills.
Don't get me wrong, you could also just materialize chained up to the bottom of a mine or in the middle of a war campaign lasting 40% of your lifespan and die in a week.
It's just since the premise doesn't say you get to refuse at least this way you'd have a good chance at just absolutely smashing it and maybe bypassing some of the real nasty stuff on the way to technological advancement.
Would you? I think that's the most interesting question in this hypothetical. Would dropping future tech knowledge in a different context just clone cultural and political progression or change course?
I think assuming industrial revolution inevitably leads to colonialism, then imperialism lets actual colonial powers off the hook. I mean, never mind that you'd probably be able to explain inflation to people and skip past some of the straight-up self-defeating resource chases, arguably colonialism is very dependent on European culture being very specifically theocratic and self-absorbed. Especially if you step in prior to the Middle Ages. Roman expansion had slavery as a common law figure, like everybody else at the time, but their incorporation of other territories was extremely not based on colonial principles, even in parts of Africa that would then be under straight-up colonial rule. Would having muskets and combustion engines have changed that? I'm not sure.
Thing is, industrial revolution bleeds into colonialism. Sure, there was colonialism before industrialization, and colonialism would look very different in a time before nation-states as we know them today, but those resources will have to come from somewhere.
Metallurgy is always where they get you on these things. You can bring stuff like division of labor, assembly lines, and replaceable parts back in time pretty easily, but good luck getting aluminum for your bicycles in any kind of quantity. Not sure how well a bronze bicycle would work, but I bet it could be done.
The problem with all of it is going to be scale. I think you're right in that you think you can just jump into the technology bit in these Yankee in King's Arthur's Court scenarios and instead you'd probably get stuck trying to revolutionize mining and material science and then die from an ingrown toenail.
Which, to his credit, Twain absolutely covers when he does the thought experiment. I'm constantly impressed that his take was "you'd cherry pick the people that are open minded enough and spend the rest of your life trying to set up an education system only to be chased away regardless because politics is a bitch".