Would you go for a boss that offer to pay you $?

Question

for you to go buy your own benefits like health insurance, retirement plans, etc. or a job that already offers you the benefits....

Answer 1

You will have to coompare the pay rates of both jobs THEN you will have to do a lot of work to compare health plans, retirement plans, etc. IF the boss is going to reimburse you for the actual cost of a health insurance plan that is not too bad of a deal. I had a job with the State of Indiana, got laid off after 15 years and found that to match the State's health care plan it is about $2200 per month. In order to get decent coverage for the family it runs about about $1000 per month. More limits, higher deductibles, etc. My new boss said if I could keep coverage limited to about $800 per month he would pay that. Better than nothing...

If you are young then a great health plan is not a great concern unless you have health problems. You can get a cheaper plan and get by. When you get older it is a greater concern.

The other problem is being disiplined enough to put money into a retirement account on a weekly or monthly basis. Build it while you are young! $2000 per year for 10 years (age 20-30, $20,000 invested) is worth more at retirement than the same as $2000 per year invested starting at age 30 until 65!!! ($70,000 invested)

Summary, you have to do some homework and compare all the variables.
Good luck...

Answer 2

Pretend you already took the deal to buy your own, then go shopping for it. If you can get a better deal than what your workplace would offer, and if you have a history of being good with money, then go for it.