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You can delegate whenever you want, as long as you know that your vote will be worth less, and that taking away a delegation takes 7 days in order for you to have your SP back (and neither you or the delegatee will have the SP during those 7 days).

You delegate on https://steembottracker.com/delegation.html, it's the easiest way. The instructions are pretty clear, I think, and if not, you can ask me on Discord.

I've delegated to a few accounts in certain occasions, and there's also the possibility to delegate to bots to sell your votes, but that's not worth it unless you have a nice amount of SP going. Otherwise, it's worth more in your own wallet because people will feel more thankful for your votes and you might get bigger votes because of that.

Overall, it's not an easy decision to make, but you can make it any time.

Also be aware that you should always have at least 50 remaining SP on your account or you could get into trouble with the bandwidth. If you have less than like 5 SP, or a similar amount, you won't even be able to retrieve your SP because delegating costs a little bandwidth and you wouldn't have enough for the operation. I used to leave 40 in my account because I'm reckless. :3

Nowadays I retrieved my delegation and have all my SP in my account to help people with my upvote. Now it's worth like 3 minimum salaries in Venezuela and I'm upvoting friends who need it. :)

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