How Much Money Is Enough? | Entrepreneur Aligned
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Entrepreneur’s Wealth Digest

How Much Money Is Enough?

Thousands of years ago, your ancestor sat down on an overturned log while the sun set on an increasingly chilly fall day. The day had been spent gathering nuts and storing them in a woven basket while watching for predators and rival bands of humans. They spent most of the day close to their family and had ample time to think about the changing seasons and what winter would bring for them all. That ancestor of yours was likely thinking about how many more days they had left for gathering ripe food before the winter closed in on them. If they already had three big baskets of nuts stored, they would think about how to get a fourth. They would consider how they only ate three last winter, but there were lots of deer around to hunt. Those deer might not be around for the upcoming winter. After your ancestor gathers four baskets of nuts, they are wondering what they will do if some of the nuts spoil or if the lake freezes too hard to fish, so they keep collecting to five baskets.

The answer for how much your ancestor needed was always MORE. Because for them, the dangers were real, and staying anxious and continuously adding more actually helped them survive. We are the product of the best, anxious accumulators who just kept at it so that they could survive. As their descendants, we also inherited those same traits.

Today, our threats are not scarcity-based. They are brought on by abundance. Instead of starvation or being eaten by a lion, our threats are “too much” of something. Too many easy calories. Too many great vacations to take. Too many options for entertainment. Too many great opportunities. Instead of hiking miles to find the one bush that still has nuts on the branches, we are surrounded by bursting abundance and spend most of our time filtering what to choose first or, worse, just gorging ourselves endlessly on everything. Our anxious pursuit of “more” is the danger today.

How does this connect to wealth and money? Well, when we think about how much cash flow we need to create or how much wealth we need to accumulate, we are looking at that number through the lens of how we spend our money. Some of that spending is important and not optional. Some of that spending is optional and adds great value to our lives and to those around us. Some of it is not necessary and does not add value. Some of it is downright harmful.

Understanding which category your spending and long term goals fall into is critical to understanding what “enough” actually looks like. So let us look at what I call The Four Spend Segments: obviously bad, hopeful but bad, necessary but neutral and genuine happiness.

Obviously bad

What do you regret immediately? When applied to reviewing your spending or plans, that one question should help identify most of the obviously bad uses of money. These can be the impulse buys or splurge purchases that you would not have made if you paused for an hour and came back to the decision. These might be recurring items or activities that feel wasteful and cause guilt. We are all pretty good at understanding this category. The key is to look back over the past few months and see if there are patterns emerging. Is it the same stuff over and over? Did they happen at the same times of the day or week? Were you doing something else that triggers using money this way?

Review the data, itemize the spending and look for patterns. Once you have a handle on it, cut spending ruthlessly in this area. Obviously bad spending does not make you happier. It just creates more drain on your cash flow and wealth.

Hopeful but bad

These get a bit trickier to identify, because your heart and head may have been in the right place. Using money here just does not create what you are looking for it to do. These are things like unused workout equipment at home, private sports coaching for a child who is not interested in the sport, vacations that you thought would create memories for the family but created stress instead or maybe the big house that you thought would solve a space problem but ended up being a repository for more stuff to purchase.

These areas really require some self examination, because you have to admit to yourself that you made a mistake of some kind. So, add them up and try to identify where the idea went wrong. Maybe the best vacation is the one with the least travel time instead of the most. Maybe you need to let your kids pick their activities and fewer of them. It really is individual to you, but looking for patterns in the mistakes you make helps you not make them again and allocate money to the things that work best. It does not mean you reduce spending but, rather, that you allocate it to our fourth category below.

Neutral but necessary

Here, we find things like groceries, insurance, needed clothing and housing costs. The point of reviewing expenses and adding them to this category is to ensure that they are fully accounted for and actually necessary. Do you need the house, cars, clothes and food that you currently use in the way you do? Would you be better off in a different house or eating out more or less than you currently do? Again, these are highly individual questions, but help you to understand how much you need and are spending for the baseline expenses of your life.

Genuine happiness

This spend segment is by far my favorite, because we get to allocate money to the things that actually move the needle for us individually and as families. There is also no judgment! If you have a second home in San Diego because the four weeks you spend on the beach as a family each year keep you connected, grounded and fit, that may be the very best thing you can do with your money. Alternately, the family with the beach house next door may consider four weeks on the beach to be a “hopeful but bad” expense, because it causes strife financially or time-wise for them. We are all unique and what drives happiness and meaning is as unique as we are. So, total up what you spend here and what you would like to spend here in the future so that you know what you are shooting for.

Now that we have our spend segments with totals on needed cash flow and future wealth, follow this formula:

  1. Cut your obviously bad expenditures to zero dollars, if possible. Reduce as much as you can in the next 90 days.

  2. Review your hopeful but bad expenditures, and describe in writing how to avoid patterns of mistakes in the future. Repurpose good ideas into the genuine happiness category if you can see how to make them work better.

  3. Review your neutral but necessary spending to ensure that it is, in fact, necessary. If not, assign the expense to the appropriate category.

  4. Look at what you need to add to your budget for things that create genuine happiness, and make a plan for that segment. If those are the things that create a remarkable life for you and your family, make them a priority, even if you cannot execute on all of them today.

You should now have a clear picture of what enough looks like for you and your family, both in cash flow and longer-term, lump sum projects. Map your entrepreneurial journey to those outcomes, and feel free to decline when you do not need it. Time is the only thing you cannot get more of, so make the most of it.


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Disclosure: Jarrod Musick is an officer of Destiny Capital and Entrepreneur Aligned, a DBA of Destiny Capital. This article is for informational purposes only and should not be relied upon as a basis for your investment, business, or personal financial decisions. We recommend consulting with your wealth advisor, CPA/tax advisor and/or attorney, as applicable to your situation, prior to implementing any new tax, legal, or investment strategy.


Jarrod was born into financial planning and solving financial problems. With his financial advisor father Steve telling stories about finance around the dinner table from an early age, the idea that everyone has a different financial situation was always there. After an early professional career spent in nonprofit and government, Jarrod came back to his roots helping people plan and invest in 2011. Since then, he has worked with individual clients, led internal teams and ultimately became partner and the CEO of Destiny Capital in 2017. With a passion for helping entrepreneurs change the world, Jarrod ultimately oversaw the creation of Entrepreneur Aligned in 2020. With both Destiny Capital and Entrepreneur Aligned, Jarrod leads teams that help people live lives of abundance where money is simply a tool to let everyone be a positive force for the world around them. When he isn’t working with the talented teams for EA and DC you can find him chasing his twins, wily trout or a podium spot at an OCR race.

Jarrod Musick


Posted: 02/06/2023

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