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Many schools of thought say, don’t invest in fixed income investments (like preferred stocks which pay 6 or 7% but have no appreciation potential). The conventional wisdom says, instead you should invest in growth stocks (like an S&P 500 index fund or Google or other growth stocks).

Now, I do understand that every portfolio does need some growth stocks for a hedge against inflation and for a future nest egg.

But one parallel I’d like to draw to shed light on this topic is the story of owning a business. Let’s say you own a T-shirt store on Main Street. You use this store to pay your bills, so your family can survive.

Let’s say your store is doing well, and it is making enough money to pay your bills. Do you know what your store is even worth? Is it gaining or losing value? Do you care? Most business owners don’t actually know what their businesses are worth. In fact, the values of their businesses are fluctuating all the time, depending on economic conditions, and other factors. I am a business owner and I meet with other business owners regularly. We almost never talk about how much our businesses are worth. We always talk about how our businesses can make more money.

Yet, with stocks, we do it the other way around. We almost never talk about how much usable income our stock portfolio is bringing in, but instead, we always talk about whether our stocks are “growing” (whether their values are higher). Like I said, there’s nothing wrong with buying stocks for growth. The problem is, you never know which stocks are going to grow, and which aren’t. And you never know when the market as a whole is going to have a 10 year slump.

Again, the T-shirt store owner doesn’t care if his store maybe is worth a bit less this year than last year, as long as he is growing his sales and paying his bills. Likewise, I choose to see my stock portfolio in the same light. Sure, I want values to creep up, but I’m more interested in the income – because it pays my bills now, or if I don’t need the money, I can reinvest it in similar or different investment vehicles.

How you look at this topic is determined largely by if you are a “now” person or a “later” person. Do you want to live an awesome life now, or wait until the years or decades pass for your portfolio to appreciate and “grow”? Personally, I’d rather live life now. Tomorrow isn’t guaranteed. So I treat most of my investing like a business – I’m less concerned about what my businesses (stocks) are worth, and more concerned about how many T-shirts (dividends) I can swing to pay my family’s bills, today.

There’s a lot more to talk about on this topic, a lot of other pros and cons to both income and growth investing. Ultimately, doing a little of both types of investing can be prudent. For me, I first endeavored to set up my income stream, and secondly endeavor to set up a growth portfolio. This is the strategy that made the most sense to me.

Lately, annoyances around my house actually bring a smile to my face. They are reminders. Reminders of a life I’ve chosen. And reminders of a life I haven’t chosen.

There’s a laundry pile in my bedroom. I haven’t had time to fold it. I used to be annoyed by this. But now, it’s a reminder that I’ve chosen to go on a bike ride or spend time with my kids.

There’s a camping trailer in my garage, taking up way too much space. It used to annoy me, but now I think of it as a reminder that having a cozy, organized, home-oriented garage isn’t my priority. Travel and adventure are my priorities.

My home phone lines are cancelled (I know, I know, the younger generation laughs at the idea of having a land line at home, but it used to be the norm). It’s no longer an annoyance to miss this – now it’s a reminder that we’ve chosen to streamline our expenses so we can live more, work less.

There are other examples, but these get the point across. Life is all about trade-offs. You can’t have it all. Even rich people can’t have it all, because they still have limited time and energy. The above examples are trade-off’s I’ve made. They make my life better, even though they require a sacrifice. But in most cases, the sacrifice isn’t really something THAT MATTERS TO ME. Instead, it’s just sacrificing a stupid societal norm, which means nothing. Such as folding laundry.

These things are reminders that I’m trying to do my own thinking. I’m trying to use my resources (time, money, energy) on what matters, not on where the herd is going.

They are the strings around my finger that remind me what road I’m taking, in case I forget. Because we all forget sometimes.

I love the work of Tim Ferriss, and on a recent podcast episode he interviewed someone who talked about choosing our failures instead of our successes. (I highly recommend Tim’s book – life changing)

We often ask ourselves, “what do I want to succeed at today?” Maybe it’s going grocery shopping. Or maybe it’s something much more grand – finishing a college degree so that you can get a good job.

What we don’t realize is, every time we pick something to succeed at, it means we are also picking something to fail at. Life has limited time, money, resources. By succeeding at something, you are ignoring something else. Maybe that’s OK; maybe you aren’t ignoring anything important. But just maybe, you are ignoring something important.

So, instead of asking yourself what you want to succeed at today, ask yourself what you are OK with failing today. This frames the question in a way that you can identify things you are ignoring in your life, which you wish you weren’t ignoring.

An example for me, is that the men in my family have always been relatively guilt-stricken over doing a “perfect” job at work. We stress about making sure we are always making the best choices and treating those who work for us perfectly. OK, this is a worthy goal. But the obsession over perfection here, may mean that I’m failing in other areas – like raising my family. Framing it this way, it helps me to see things in a new light, and to realize that actually, I’d rather succeed in raising my family and fail sometimes at work. I’m not talking about making any really bad decisions at work or being lazy, I’m just talking about dumping the perfectionism. What are you willing to fail at today?

As you can see (below), this week I succeeded in buying my kids two awesome new mountain bikes. This means I failed at putting that $1000 into a retirement account. But when I frame it this way, it’s easy for me to see which I’d rather fail at. I’d definitely rather fail at investing than fail to pass on to my kids the joy of mountain biking, my favorite sport.

Bonus topic: The question of what to fail at becomes harder and harder to answer the older and more successful you become. When you are young, it’s easy to put off big purchases because you don’t have kids yet, and you don’t have any money, and the goal of getting financial stability is all-encompassing. You save, invest, buy a house, eat beans. Great. But as you get older, the numbers become more abstract. Will it really make that much of a difference to put 5% more in my retirement account this year? Will that be better than buying mountain bikes? Not such an easy question. Because saving for retirement is a very volatile proposition, and depends on a lot of things like – how the stock market will do, how long I will live, etc.

Therefore, since I can’t predict the future, I simply have to choose what I want to fail at today. I can’t succeed at everything. Today, I succeeded in getting my kids on some dirt trails. Honestly, I don’t really care what I sacrificed to achieve that goal, because it was worth it!

(and yes, maybe disc brakes for a 5 year old is a little overkill, but the bike is geared fantastically for Tahoe hills and it has 2.8 tires! Duh!)

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I’m not able to pay all my bills by passive income yet. But that doesn’t mean I haven’t made any progress.

In theory, we know that passive income can help you pay your bills. But what does it actually feel like? Well, here’s a glimpse I’ve had this month…

I’ve been trying to put work on autopilot this summer, to take a lot of time off and hang out with the family. At the end of this month, I realized I hadn’t gotten a lot of work done and the finances were getting squeezed a little. Just as I was thinking, “man I better go do some projects,” I checked my online banking and a few bits of passive income had just hit my account from various investments… and bam, just like that, my spreadsheet was healthy again. This was a cool feeling. You can tell someone how fun it is to ride a bike, but until they’ve actually DONE it, it’s meaningless. I think the same is roughly true for passive income – actually feeling it means so much more than just talking about it.

I still have a long way to go before the numbers are more substantial. But I’m glad I’ve got some emotion behind my motivation now. That was a super cool feeling!

I care much more about analyzing my finances in a theoretical “bad year” than I do in a good year. Why? Because the bad year (a low income year) is the one when my lifestyle would be threatened. In the good year, nothing is threatened. So, I think of my good years as “future proofing” seasons when I do what it takes to get life ready for the inevitable bad income year.

This is in contrast to most people who look at good years as a time to prepare for retirement. For me, the primary goal in a good year is to prepare for the bad year before retirement. The secondary goal is to prepare for retirement. And the holy grail is to do BOTH at the same time, which, thanks to this awesome discovery, is possible.

Why am I so worried about the bad years? Because…most people, if they have a bad year, either have a TON of stress, or they have to go work MORE, or in CRAPPIER jobs. I don’t want to do either. In a bad year, I still want to be able to enjoy life and enjoy my family. So preparing for the bad year is super important. I’m self-employed, so my income varies, so it’s even more important. But even someone with a regular “job” could lose that job and be forced to get a terrible job, if they aren’t prepared for the bad year.

So, what are some things you can do when income is good, to prepare for the bad year?

  • Pay down debt
  • Get reliable cars
  • Make big house repairs like a new roof, so these don’t hit in a bad year
  • Develop streams of passive income
  • Streamline and consolidate core expenses
  • (these are just some examples)

Another important thing to do, is to optimize your tax situation for the bad year. One thing I’ve been focusing on a lot is trying to hold investments that pay qualified dividends, in my taxable account. This is because, in a bad year, my tax bracket will be lower and these dividends will be taxed at a rate of ZERO! Yes, the US Government currently taxes qualified dividends at ZERO, if you fall below a certain tax bracket.

On the other hand, T-IRA income is always taxed as ordinary income, so you should go for the highest return investments, not those which are tax advantaged.

So, knowing how to invest and plan in good income years, in preparation for the bad income years, is an important step. It’s kind of like, if the sun is shining and the weather is good, you start preparing for winter. You need to know what winter will bring – cold, snow, wind. You need to know how to prepare for these things. Same thing with money. You need to know how your tax situation will change in a bad year, and how to optimize for that.