Now that I’ve been investing for 15 years, I find myself asking all of the time – when will I be able to stop?  We’re having a family and expenses definitely are rising slightly each year.  We keep investing into the stock market and climbing towards financial freedom.

This article focuses on the topic of knowing when to stop investing and truly start living.

15 years of investing

15 years ago I set out on a mission to reach financial freedom.  15 years ago I set a goal to be retired young.  I wanted better for my life and future family.

Here we are, 15 years later, still investing.  What happened?

Life.

Life changes.  You get married, you have kid(s), you change careers, you change location, you change what’s needed for others.

There’s no question, if I was not married or with a family, there’s a chance I’d be financially free now.  BUT I pursued my family goals and passions, getting married and having a family.  Now, I want them and everyone in my family to bear the fruit from investing – granted it’s taking longer.

These are thoughts on “paper”, so I have to apologize for the possible randomness.

Over the last 3-4 years I’ve also had the pedal down, investing more than I ever have in my life, making every dollar count, while also saving for a soon to be bigger house, as my 1,400 square foot house isn’t cutting it anymore.

The passive income from dividend income has essentially more than doubled in those years, and I’ve never wanted to be financially free moreso now than ever.  For my son.  For my wife.  For my mom.  For many others.  Prove the naysayers wrong, all of them.

But if I have been investing for so long and my passive income is growing at a fast clip – why don’t I just stop and start living?

Why I haven’t stopped investing

The unknowns.  I’m being honest.  So many unknowns when it comes to “hanging it up” like MJ or Kobe.  I am sure LeBron feels it.

The unknown of when we will find the right house to move into, with record high inflation, higher than recent history interest rates and sky rocketing real estate prices.

The unknown of health.  What adventures we want to go on and accomplish, our family’s health and desires, so many items.

The unknown with what we can’t control.  The tax code on dividend income, will the stock market continue to average 7%-10% each year or will other asset classes rise up and shun it all away?

There’s also fun to investing.  It’s fun knowing that you can be so disciplined, so consistent with earning, saving, investing, repeat.  Seeing the numbers rise up, day in, day out, week in, week out, month in, month out, year in and year out.

The last obvious reason – we haven’t gotten to our goal, yet.  We haven’t hit that cross over point – based on the above.  The house being the big thing.  We haven’t seen the dividend income cross over the expected monthly expenses yet.  Therefore, I still continue to invest.

When to stop investing and start living

The obvious answer here is the cross over point.  The cross over point when passive income exceeds monthly expenses.

I then go and run investment calculators and returns, the numbers will and should be staggering in 10, 15, 25 and even 50 years out.  However, so much pressure to get there – NOW.

When will I stop investing?  In the short-term – if life takes a few different turns where any income needs to be re-allocated to other important areas of life.  Until that occurs, I’m not stopping.

In the medium term – I’d like to take my foot off the gas with the 401k.  Something about putting so much in for years and years, that – without conversions and ladders – could be locked up until 59.5 years of age is concerning.

In the long term – I can envision any excess income over expenses from being financially free to be invested into family members futures, non profits, and the place where I live with experiences we want to have.  THAT will be the primary investing I will be doing in the long-term.  Anything extra will surely go back into the investment portfolio.

If you haven’t noticed, no timelines were given above.  Given I’m still in my md-30’s gives me hope that only a few years left of the short-term and I’ll be entering that mid-term soon.

conclusion

After all of those thoughts, statements, desires and passions here I am keying on this keyboard, putting it on paper.  I had a goal at 20 years of age to reach financial freedom at an early age.

I can guaran-damn-tee that is going to happen.  That goal and desire has NEVER changed.

And for that…

I’m not stopping investing.

-Lanny