I retired a bit over 4.5 years ago and have been getting my income from an SPIA (purchased at retirement, at age 59 with funds from my retirement portfolio) along with a small VA disability check each month, including retirement portfolio withdrawls.
My personal "psychological challenge", if you will was to put aside the traditional 4% withdrawal guidance, which is touted in many articles/blogs.
It might be a good target for those that retire with all their income sources (pension, SS, SPIA's, etc.) starting on day one of retirement, but for us the idea did not work as advertised.
While DW was to retire the same month as me she decided she was not emotionally ready, and still remains in "contribution mode" today. However, our plans were as such that she could have retired back in early 2007 as I did, or retire tomorrow if she wishes.
Regardless of that, our planning was always based upon not having any income (beyond the SPIA/VA benefit) from age 59 till age 65, when her two small pensions would start.
Additionally, our plan is based upon the SS option of her drawing at FRA (in just over two years at age 66), my 50% spousal claim at that time (we're the same age - within a few months), and delaying my SS till age 70 (primarily for her benefit, assuming I die first).
While our plan shows current withdrawals more than doubled that 4% goal (assuming she retires tomorrow) it really doesn’t mean a thing in our case.
Why? Simply because in just over six years (when I turn 70, and all our income sources come "on-line"), our retirement portfolio withdrawls drop to less than 3%, even accounting for funding most of our early retirement expenses outside of most benefits. That includes the fact that our annual portfolio draw will be 75% less than today (assuming we were both retired).
Sure, we could adhere to that 4% by cutting back our standard of living to much less than we had just before we retired, but why? If we would, we would (at age 70) have a withdrawal rate of a fraction of a percent, while living a lifestyle before that time much less than what we planned on.
That's one point that is often overlooked in planning for retirements that start much before any benefits start and you need to draw down assets at an advanced rate - contrary to advertised "good practice".
Just some facts from our situation, concerning the OP's question - and no, it was not hard psychologically to do so. You still have income, but the sources are different as you age, rather than depending on a j*b. While we were of the 4% "rule", our planning and expectations showed that the 4% guidance need not be followed from day one of retirement assuming you ER. Our plan was on solid ground, and the last 4.5 years have confirmed our planning...