Welcome to the Daily Chizuk. The Midrash tells us that Yosef HaTzaddik was punished with two extra years in jail because he asked the Sar HaMashkim (chief cupbearer) to help him get out. All the Mefarshim (commentators) are bothered. Why should Yosef be punished? All he did was make a Hishtadlut (effort). Chazal actually learned from a pasuk (verse) that we have to put in our own efforts in order to receive help from Hashem. As it says, "You have to make an asiyah (action), and then Hashem brings the blessing." So what did Yosef do wrong? It's true that the more you trust in Hashem, the less effort you have to make. But this was seemingly a very small amount of effort: just asking someone to mention his name to Paro. The Chafetz Chaim says, "If Yosef would have just said, It would have been okay. But he also said, He asked the Sar HaMashkim for help," and then he reminded him again. Someone on Yosef's level should have been satisfied with one request. Rabbi Dessler writes, "Of course Yosef was allowed to ask for help. But as Rashi says, for a few seconds, he put his hope in the Sar HaMashkim." We're allowed to make an effort, but we have to believe the people helping us are just messengers of Hashem. If this one doesn't work, Hashem can just as easily send me another one. We never have to put our hopes in man. I'll give you hope. Hashem has millions, millions of messengers.
I saw another Peshat (plain meaning) in the Sefer Ki Ata Imadi. He says that Yosef told the Sar HaMashkim, "You won't be taken out of jail for another three days." Therefore, Yosef shouldn't have asked him for help until then. Maybe Hashem would have saved him another way before that. Either way, everyone agrees that Hishtadlut is necessary. It just has to be done the right way. You shouldn't do extra Hishtadlut, and you should know that whatever you do, it's B'yad Hashem (in Hashem's hand).
Mesilat Yesharim writes, "A person is obligated to do something to make a parnassah (livelihood). But once you did something, you fulfill your obligation. Then you have to trust in Hashem that He will give you exactly what was destined for you to have." Rav Zundel of Salant said, "We have to make a Hishtadlut because Hashem is not going to make an open miracle for us. But once you have done enough that it will no longer look like a miracle for you to get your parnassah, then you have fulfilled your obligation." All you need is a normal effort. In fact, the Chovot HaLevavot says, "Since all you're doing is opening a pipeline for Hashem to send His blessing, a person should choose an occupation that fits him the best: do something you're good at and something that you'll enjoy." But whatever you choose, while you're working, you must put in your full efforts. The Rambam writes, "A hired worker has to work with all of his strengths, as it says by Yaakov Avinu." The Torah doesn't preach laziness. Put in your normal hours and work as hard as you can. But then it's back to learning Torah, doing mitzvot (commandments), doing chesed (kindness), and helping your family. After you made your Hishtadlut, there's no mitzvah to worry. It's counterproductive. Hashem is in charge of your parnassah, and it's not your efforts that produce the blessing. The efforts are just your tax. Once the tax is paid, the blessing can come in many ways.
Rabbi Moshe Shapiro once sent a boy to try to raise money for his yeshiva. The boy tried very hard, but he came back with nothing. A couple of days later, a wealthy man came to the yeshiva and unexpectedly made a very large donation. The rabbi went to the boy and thanked him for all of his efforts. The boy said, "I didn't even ask that man. Why are you thanking me?" The rabbi said, "We had to make a Hishtadlut, and you did it for us, and now Hashem sent down the blessing this way."
The goal is to serve Hashem with peace of mind and trust in Hashem that He'll take care of you. If you feel you put in enough effort and made a pipeline for Hashem to send His blessing in a normal way, you did enough Hishtadlut, and now you could spend more time with Avodat Hashem (service of Hashem). But if you think, "Maybe I didn't do it. I didn't do enough. I have to do a little more," then you might need to do a little more until you reach that higher Madrega (level) of more trust. There is no mitzvah to do extra work, but there is a mitzvah to have Menuchat HaNefesh (peace of mind). When it comes to Hishtadlut, it's not one size fits all. We have to remember, Hishtadlut is not a goal; it's a means. The goal is to serve Hashem, trust in Hashem, and always feel that He's taking care of you. Shabbat Shalom.