When my husband retired he had a few extra bonuses that help him retire early. He was paid for his 10 weeks of paid vacation he banked. He also had a loan against his 401k when then came due or was recorded as income. I tried to warn him and he would not listen to me. So when it came to tax time he did not have enough withheld so we had to pay over $15,000 out of pocket. He retired in July and this was of course in April when we had already spent the money. Before you retire talk to an accountant or financial advisers so you do not run into anything like we did.