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Why Do My Side Hustles Always Fail?


Chapters

0:0 Cal's intro
1:0 Lifestyle Centric Career Planning
2:30 Drastic changes
3:50 Money as indicator

Transcript

All right, one last question. This comes from Diamond Michael, a writer from Denver. So question 13, 13 questions for 2023. This is question 13. Diamond Michael says, over the years I have had numerous situations where I've tried to launch a freelance business idea with little or no capital. At the point in which the resulting financial scarcity becomes too much to bear, I resort to a regular full-time or part-time job in order to yield a steady income.

The problem is it seems like the more well-paying my job, the greater the expectation in terms of work hours and energy investment. This in turn reduces my time and energy bandwidth to devote to the deep work tied to what I quote unquote want to be doing. So I'm curious as to what your advice is in resolving this dilemma, where my energy and attention are directed in two different directions.

All right, so Diamond Michael, we have to get way more systematic about what you're doing here. Two pieces of advice to offer. First is gonna be the piece of advice we've been saying throughout this entire episode. Lifestyle-centric career planning. You are throwing energetic darts at the wall here. You're like, I don't like my job.

Like, let me just quit and do the side hustle. Oh, the side hustle's not working. I need a job. What's the highest paying job? I guess I'll take that job. You're just bouncing back and forth. Sort of instinctual grabs from one thing to another. Let's get more systematic. Develop a clear vision of what you think a life well-lived looks like.

All the different aspects of your lifestyle, the properties of your work, but the properties of where you live, your community, the different types of things you're involved in, all of the attributes of a lifestyle vision that really resonates. Get this really clear, and then figure out pragmatic paths to get there.

This will inform what you need out of your job. Where you're gonna live, what your lifestyle's like, how much that costs, what type of properties you get out of your work. This will help inform what type of job you need. That's where you might figure out, wait a second, I can use my expertise to get a freelance position in the same industry.

Allows me to move here, ski 50 days, 50 weeks a year, not 50 weeks a year, 50 days a year, I don't know. 50 days a year. And have flexibility. Great, this is the right path forward to my lifestyle. Or I need a whole other, I need to leave my industry altogether and start my own business.

This is what's gonna help you answer that question. Because I think what's happening now is you're just fetishizing the idea of a side hustle as being drastically different than what you don't like about your job. And if it's drastically different than what you don't like, then maybe you'll drastically like it.

That syllogism is flawed. You need to be working backwards from a specific lifestyle, detailed in terms of properties of your life, attributes of your life, and then figure out a career strategy that matches that. If it turns out after you do this calculus that starting your own business, or having a side hustle that allows you to really pull back on your current work, and it makes the ends meet.

Oh, I could be freelance twice a week. That's not quite enough money, but if I had a side hustle generating $30,000 a year, now the numbers work fine. If you need some sort of side hustle or full-time business to make this vision work, then we're gonna get to my second piece of advice, which comes from my book, "So Good They Can't Ignore You," which is the notion of using money as a neutral indicator of value.

You don't quit your job until the new thing is making enough money that you don't have to worry about money when you quit your job. Now, it could still grow more when you give it more attention, but it has to prove itself. Your side hustle or business idea has to prove itself by generating money.

People will always tell you, "What a great idea, Diamond Michael. "Great, do it. "Follow your passion. "You be you." It's easy to give compliments. What's hard is to get people to give you money. They will not give you money unless they actually like what you're offering. So use money as your neutral indicator of value.

When your business or side hustle idea is generating sufficient money to support you, then you make the change in your other job. And if it's not, that means it's not a good business. It's not a successful side hustle. Don't flee that feedback. That's the most realistic feedback you're gonna get on the viability of your option.

All right, so those are my two pieces of advice. Do lifestyle-centered career planning instead of action-based career planning. Quitting will be exciting. Disruption will be exciting. My own job is better than one where I work. That's action-based career planning. That's just giving into your gut and fleeting emotions in the moment.

Be more systematic. And if that plan does point towards the need for you doing something on the side or something on your own, let money be your neutral indicator of value. If people aren't paying you for it, it's not a good idea, no matter how much you think it is your dream.

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