The Hassle for Money Dilemma

hassle vs money

The hard part of dealing with reality is the constant trade-offs we have to make. Yes, we want it all, but too often that is not the choice before us. Choosing one thing means giving up something else, whether that is opportunity, time or attention.

When we are faced with deals that come before us, we have the dilemma to consider between hassle and money. A trade will happen at a certain cost. The question is whether it is worth it.

There are four general outcomes when it comes to making a rational business decision for yourself. Here are my thoughts on each:

1. High Money, Low Hassle

This is the ideal situation. Great clients that are truly partners and allow you to get your work done and drive to results fit this bill. So is highly innovative technology you own and can lease out without any significant support, complaints or drama.

This is the kind of deal you want to take frequently. If you let circumstance dictate your outcomes, then this cream of the crop kind of deal will likely be elusive. It takes intentionality. Profile who you are seeking to do business with and position and pursue them with the right messaging, attraction and invitation.

2. Low Money, High Hassle

These are bad deals. If you take these frequently, you won’t get anywhere for the long-term. Being cheap and working hard with headaches can be a painful existence. You can easily drive to burnout when there’s no reward and only problems.

Commodity businesses where price is the crux point of every deal and demanding customers wanting the world from you are to be avoided. Little reward with lots of stress are deals to avoid. You can use your time, attention and resources towards more fruitful ventures.

3. Low Money, Low Hassle

If you hosted 100 websites without any support, this is passive money, albeit not much. But then again, there’s the hassle of the occasional downtime or mini-crisis.

You can judge the deal with indifference in this category.

If there’s a path to something bigger, I think taking the deal is worthwhile.

If it’s merely something you stumble on without any upside, then the cost can be something else to manage in your life. And you only have so much attention. Your net cost may be small hassle from appearances, but there are always costs under the surface. Consider how real that is. Continuing to take a large amount of deals that fit this category will keep you treading water for many years to come. There’s no end game. But then again, the low hassle may be worth it if it truly is without work, resources and attention that cost you other opportunities.

4. High Money, High Hassle

This is the dilemma deal. Do you take the big money for that eccentric and problematic customer? Do you build that platform which will get a lot of first mover advantage but also require intense development and maintenance?

If you are ok with money and stress, a business model where you are in these kinds of deals frequently may be ok for a while. The wear and tear on your psyche and health may be able to take it for a few years.

And if your supply and demand equation necessitates you give up a bit more to get more leverage for right now, then this kind of deal making may be worth it for a period of time.

I don’t like stress. But I understand you may have to have stress for a time to get where you want to go. The question in this deal is whether you have an exit, next step or bigger vision to get to. Fill your reserves and work in parallel on building a model that is more sustainable.

Keep Moving

We are making trades every day on the type of deals and relationships we choose. Whether that is with employment or servicing customers, you are making that trade.

We want High Money, Low Hassle deals. That would be ideal. You likely take many types of deals. On the questionable trade-offs, consider building a plan so you minimize the need to compromise and have a bridge strategy to move towards low stress with high payoff.

What are your thoughts on this?

Published by Don Dalrymple

I partner with founders and entrepreneurs in startup businesses. I write and consult on strategy, systems, team building and growing revenue.

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