You Need A Side Hustle and 15 Terrible Ideas

Note: This post grew pretty lengthy, so I broke it up into three pages:

8 Reasons Why You Need a Side Hustle
The Problem With Side Hustle Lists
15 Terrible Side Hustle Ideas

Navigation is also at the bottom of each page.

Do The Hustle

I define a “side hustle” as: any income you actively make outside of your primary occupation.

Side hustles differ from a part-time job in that a side hustle will tend to have some flexibility in the commitment and duties, and it will hopefully align with your interests or general happiness.

I’m going to give you eight reasons why everyone should have a side hustle,  then we’re going to have some fun with how ludicrous the business of making lists of side hustles has become, and finally I’m going to offer 15 terrible side hustle ideas—hopefully one of which you might find appealing enough to try.

8 Reasons Why You Need A Side Hustle

  1. Redefines Your Value of a Dollar
    • We tend to get very accustomed to our primary salary and lifestyle expenses. If you aren’t paid on commission, then the quality or quantity of your work will fluctuate from month to month, but the money you’re paid stays the same. As this occurs, you stop appreciating the value of a dollar as there is no longer a direct connection between performance and pay. If you want to go out for a $150 steak dinner, it is difficult to quantify that in terms on how much work you do. However, if you side hustle, that $150 steak dinner suddenly becomes: mowing 10 lawns, writing five articles, delivering 40 pizzas, completing 32,000 online surveys, etc. When a hustler makes a purchasing decision, they can relate it to the true work that it takes to acquire the good, and the decision is much more informed.
  2. Gives an Appreciation for Entrepreneurship
    • This is somewhat in the same vein as above, but more directly related to the work, rather than the money. If you’re working for somebody else, then by definition you are not an entrepreneur (at least not in that occupation). However, once you strike out on your own, every success and every failure is 100% dependent on the amount of work you put in (and a little bit of luck). There is no hiding. At my primary job, I could probably do nothing for a week (Dear Employer: I will not do that, I’m just saying I could do that) and nothing would happen. I’d still get paid the same, I might push a deadline or two, but otherwise nothing will happen. At Retire29, or with my SeekingAlpha writing, if I take a week off (like a did earlier this month during our vacation to Orlando), things start going off the rails. Pageviews decline, rankings fall, AdSense evaporates, people stop caring, etc. Nobody is going to pick up my slack. This is the double-edged sword of entrepreneurship, you reap all the reward, but suffer all the loss.
  3. Diversifies Your Income Base
    • You never know what will happen with your primary job. You could get disabled, or laid off, or downgraded. Despite our best efforts, businesses change and employment will change with them. If you can diversify your income streams through side hustles, where your efforts generally correlate with your income, you are no longer as vulnerable to any one source of income.
  4. Creates an Avenue For Business Development
    • Sometimes, if a certain side hustle works out, it can grow to a point where there is an opportunity for scaling it up to a primary occupation. My wife wants to be a life coach, and is currently pursuing that certification. I’m working toward my CPA and may go after a CFP following that. Given the close alignment that life coaching and financial coaching have, we’re considering partnering up in an LLC somewhere down the line to offer a spectrum of location-independent advising, coaching and consulting services to supplement our retirement lifestyle. This would have never been a conclusion of ours had it not been for lessons I learned at Retire29 and throughout the financial independence blogosphere.
  5. Fosters New Skills
    • Not that unlike developing a business, but side hustles can develop and hone a particular skillset that would otherwise go ignored. For me and blogging, that skill is undoubtedly writing. I look back at some of my earliest blog posts (Archives here), and I’m amazed at some of the horsesh*t that I willingly hit “Publish.” For other side hustles, you will undoubtedly improve people skills, organizational skills, small business accounting, social media marketing, some computer coding, and the list goes on.
  6. Makes Life More Interesting
    • Anything that takes you out of the routine of life tends to make things more interesting. I can no longer count on one hand the number of all-nighters I’ve pulled trying to write an article or blog post. Variety is the spice of life, and a side hustle introduces new challenges and opportunities will change your daily routine and introduce new conversations.

  7. Cultivates Your Passions
    • Unless you are doing exactly what you want to do at your primary job (and you’re not), then a side hustle can be a way to earn money doing something you have a true, deep passion for. This isn’t a side hustle of mine currently, but maybe one day I’ll write weekly Start/Sit articles for Fantasy Football–something that I simply love doing. Your side hustle can be surrounding something you actually really enjoy. Enjoy animals? Walk Dogs. Like the outdoors? Offer guided hikes at a State Park. Love Fitness: Be a trainer. Any one of those ideas will sound awful to most people, but you only need one thing you otherwise really enjoy, and then find out a way to make money on it.
  8. Brings Retirement Closer by Putting More Money In Your Pocket
    • This is certainly the most noticeable reason, and likely the one that drives you initially. Most people have a lifestyle cost that paces their income. When you add some side hustle income to the mix, you don’t need that money—it’s just a bonus. You can take whatever funds you make and it goes immediately into investments, perhaps through a SEP IRA or other tax-advantageous vehicle. There is no lifestyle adjustment for this additional savings, so it’s pure gravy. More than that though, is the tremendous power that a little side hustle income has during retirement. Every dollar you continue to earn throughout retirement directly offset current expenses, which significantly reduces the burden on your invested assets. I talk about this at length here. As a quick example, at a 4% dividend yield or 4% safe-withdrawal-rate, for every $1 you can make per month, the necessary size of your nestegg by drops by $300. For those looking to retire very young, the power of a side hustle is a game changer in retirement planning. I’m shooting for just $200/mo in side hustle income in a few years (something I’m very confident I can do); that income means I need to save about $60k less than I otherwise would have.

So, are you convinced? You’re clamoring for a nice long list of side hustles so you can get started. Well, let’s keep going!


    • Scott,
      Come back! I never get feedback like this and I love it! I removed that second ad that was up top and decided to place it elsewhere. I’d hate to think somebody thought Retire29 was covered in ads. I hope it’s a little better now.


  1. Could you tell me a bit about how you treat your seeking alpha income for tax purposes? Do you put all the revenue into a sep ira (I don’t know if this is possible. Maybe after incorporating?) or do you take the money in cash and pay loads of taxes (federal, state, fica, …)?



    • Hi Darren,
      I just started writing this year, so I haven’t filed taxes yet. But, I plan on writing off several costs to offset about half of that income (depreciation on laptop, portion of internet cost), then with the remainder, I’ll recognize it as ordinary income and I expect I’ll be owing 15.3% (2.9 Medicare and 12.4 SS) on that income, plus income taxes.

      However, this sounds like a good post I should make. I’ll do one early next year when I file discussing how it all shakes out.

      Thanks for commenting!


  2. Good post. I’ve found that my side hustle has turned into some pretty big cash, but not the way I intended.

    I retired early (at 50) after selling my software biz. To keep my yearly draw to 4%, I figured I needed a little side hustle income to allow me to play heartily in retirement.

    So I started a blog and started developing mobile apps. My mobile apps are bringing in some monthly cash but based on the amount of time I put into them, it’s like minimum wage.

    However, I put lots of time into driving traffic to my blog and building my Twitter following (now over 21,500 followers – twitter handle is @2hourappreneur).

    I posted a blog post about how I built my following and a friend I worked with years ago asked if I could help him do it for his blog for $50 an hour. Cool, work a couple hours a day and bring in some decent side hustle money. That has worked out great.

    Two weeks ago, I was called by another friend I worked with in the past and he wants to me to help his new company develop a software solution. I told him I could only oversee and advise it, work 2-3 hours a day max. Rate: $200 an hour. Now that’s some good side hustle cash and I should be starting that engagement in November.

    It’s funny how a little blog turned into this type of cash and allows me to work a couple of hours a day and play the rest of the time.
    Steve Miller recently posted…Don’t Worry Be HappyMy Profile

  3. Great read, always looking for extra ways to make cash around the office. I just wanted to share something I’ve been doing recently. I run an office and have noticed that unused toner was piling up in storage. Looked into returning but that was no good. Tried out the site and was impressed. They had quick service and that payout was nice.

  4. Hi terrific website! Dooes running a blog like this require a large amount off
    work? I’ve virtually no understanding of computer programming but I had been hoping to
    start my own blog in the near future.Anyhow, should you
    have any ideas or tips for neew blog owners please share.
    I understand this is off subject however I simply wanted to ask.
    Cheers! recently posted…marketersmedia.comMy Profile

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