Retire or wait?

As a young guy in my 20's, I would daydream at my job about retiring, what it would look like, how much money would I need, where would I retire?  I would even make the $ calculations in my head, how much to save, growth rate needed, etc!  I really didn't like my job loading trucks, and daydreaming was the only way to get thru the day sometimes.😂

In my 30’s I was married with 2 kids and my time and money was focused on providing for the family and how I was going to pay the bills.  Retirement was so far away that I didn’t really think about it, much less save for it.  I was so worried about paying the mortgage, car payments, insurance, food, utilities, etc that saving for retirement was not a reality.  I mean literally everything I earned was spent.  My wife stayed at home with the kids, a decision that I don’t regret for a second, but was such a strain financially and mentally.  It was cheaper for my wife to quit her job than work and pay for childcare.  Such a tough situation, but everyone with kids in this country have to face the same type of scenario.  If you are fortunate enough to be able to afford to do it, congrats to you!

In my late 30’s going into my 40’s, we were in a better rhythm financially and I was able to put more aside for retirement.  I maxed out my 401k when I could, and we also did a spousal IRA.  It was something I really couldn’t afford to do TBH, but we had to do something.  I was starting to think that I would never be able to retire and would work until I die.  Seriously.   We would put a lot of expenses on credit cards, then I would try my hardest to hit bonuses and pay them off.    It was such a letdown that I worked my ass off, and when I would get that big check, it would all go to pay the CC off.  Then we start the circle all over again.  Exhausting mentally and physically. 

In my early 40’s I was really trying to focus on saving, not investing, just saving.  Kids were getting older, I was moving up the corporate ladder and making a little more money.  I was so over corporate that I was daydreaming again of starting my own business.  I spoke to wife about it for years, and I think we were finally both on the same page, and the timing was right to give it a try. 

So, I go out on my own in 2016 and I put everything I got into it.  I’m talking 7 days a week, 10-15 hour days.  Long story short, failure was not an option.  Slowly but surely, I picked up clients.  Revenue started growing year over year, and I was freaking out a little bit less and was actually able to get a good night sleep.  Lot’s of sleepless nights and numbers/scenarios running thru my head always to where I would only sleep 1-3 hours a night, then crash every few days.  It was real challenging.

Now, almost 8 years after starting my business and 20 years in the industry, I am pondering retirement again, but this time for real!  Never wanted to work until my 60’s and then try to make the best of the time I had left, IF healthy!  I always wanted to retire by 55 and try to travel and enjoy my time before I got too old to enjoy it.  All that hard work and sleepless nights may be off.  If my current business ventures work out, I can retire at 52-53 years old!  Just to write that seems crazy, but all the math I ran checks out.  I have been to 2 different financial advisors and had plans made, they all show the retirement scenarios.  I still have a way to go, but I can have my house paid off, no car payments, no CC debt, strong bank accounts/investments and rental properties that are producing income that will supplement my retirement if it works out.  The biggest cost is going to be health insurance, but as a small business owner, I have been paying an insane amount for my family insurance, so I’m used to it, I guess.   Kids will be half-in, half-out of the house, so there will be some extra expense on that as well.  Both are in college, one will graduate this year, the other in 3-4 years.  I have been saving for their education since they were little, so there is some money to help with that.

I think about retirement all the time, but don’t want to get too much ahead of myself and be disappointed if it doesn’t happen.  My financial advisor says I should keep working in order to create a bigger legacy to leave my kids.  I have been working for my kids my whole life!  With what I have, I think I will leave a pretty good legacy already when I die.  I’m not really too concerned about leaving a legacy, I think what I have done has never been done in my family or my wife’s family, so I think we’ve already achieved more than we both dreamed about.