A constant theme and recommendation of this brand will be that most people should probably keep their primary career for much longer than most personal finance advice would tell you.


  1. For most people, your primary career is your career because you have likely built up an associated skill set. Maybe it’s a number of years of industry experience or a degree or two in the field. This is valuable. Even if you’re unhappy in your current job or don’t like your boss, consider that you have built up a competitive advantage here, think carefully before you give that up.
  2. It’s probably your largest income stream. You need that income stream to buy and/or build additional income streams. If you try leaving your job to try to start or buy a company, you will be surprised if you try to go out and get bank financing that they probably would have preferred you get your job! This is because for smaller loans (think under $5M) banks will almost always make you sign a personal guarantee … so they like to see that there is money coming in.
  3. There are social and cognitive benefits to interacting with other people on a daily basis and facing intellectual challenges. Research shows that people who retire early face cognitive decline earlier and faster than those who do not. What are you really going to do if you retire at 40? Sit on your couch all day for the next 40 years?
  4. Once you have additional income streams and/or enough wealth that you can walk away if you want, you will find everyones #1 career complaint … office politics … a lot less irritating. Trust me. It will still be there and you will still be annoyed at times. But the secure knowledge that you don’t “have” to be there will make these games a lot less aggravating and stressful. It will become more like a fun game you’re playing to see how far and how high you can go in your chosen career field. And, if it does get bad, you will have the actual ability to walk away and find a new job/career.
  5. Similar to above, once you are able to walk away if/when you want, you will be in a much stronger negotiating position when it comes to pay and vacation. You will be able to push a little harder. On average, you will probably be rewarded for this stronger position (although, if you don’t play it right this could always go against you). So, again on average, you will receive more compensation for less days worked, not bad right?
  6. Of course, if you’re really miserable, or you’re not making very much money, it’s acceptable to switch primary careers to something else. Once you’re making more from your main side hustle than your primary career, it might be time to think about if you should switch and make that side hustle your new primary job. Many side hustles are inherently unstable businesses, though, so you should have at least 1-2 additional streams of income as well.

So, when should you start building your first side hustle?

Once you’re making $200K/yr+ in your primary career, it’s time to start building the second source of income. (Note: you can and should start investing in truly passive income, like index fund ETFs, long before this. I’m referring here to a second source of income that will take a lot of effort).

Why $200K+? Primarily two reasons:

  1. You should have enough after taxes, living expenses, and retirement contributions to invest in this new side hustle.
  2. $200K is very achievable for MOST people (read: not everyone), so your efforts are best spent getting there quickly before diverting time and energy to something else. It’s achievable for MOST people because this is still a relatively entry level compensation for many professional class careers like a doctor, lawyer, or a banker. Many Tech jobs can easily make this too, if you can demonstrate the right skills. If you aren’t making this, you could, for example, go get a Top 25 MBA and have a reasonable expectation that you would make $200K+ in your first year out of school.

Keeping your primary career also fits with a maximalist lifestyle, you keep the high income coming in while you build additional income streams.