Free yourself from the grind
January 17, 2017 8:29 AM   Subscribe

Who are the best gurus and best resources for "freeing yourself from the 9 to 5 grind"? Everybody and his brother has a book on how to set up an online business and/or multiple streams of income that will allow you to work from anywhere on your own schedule. Who are the best?

Right now I'm reading Chris Gillabeau's The $100 Startup and liking it pretty well. I would like to find other resources that would give me ideas, inspiration and encouragement for striking out on my own. Googling is no help, seems like there are a million people who believe they are qualified to teach me how I too, could become successful like them. Amazon's recommendations based on the above book contain a concerningly high number of 2.99 Kindle books. I'm not sure how to sort out the good from the meh.

Books, blogs, podcasts... I'm interested in whatever you got. Just trying to get an idea of who is well thought of in the field as opposed to the fly by night guys.
posted by Serene Empress Dork to Work & Money (18 answers total) 58 users marked this as a favorite
Pat Flynn's Smart Passive Income is the way to go, especially if you're looking for information about passive income and affiliate marketing. He's no joke and well regarded in the online business world. Good luck (I'm in the same boat as you!)!
posted by Nutritionista at 8:37 AM on January 17, 2017 [4 favorites]

Ever notice how people who claim to make a bunch of money doing X always seem to be selling something that teaches you how to do X? Why don't they just spend their time doing X?
posted by scottatdrake at 8:57 AM on January 17, 2017 [31 favorites]

Writing and selling a book is, for some people, one MORE source of income, with little ongoing work once set up on a website and no overhead. I'm hoping to be directed to those people and be steered clear of the guys whose only idea for an online business was to write a book about how to make money in an online business. Hence the ask.
posted by Serene Empress Dork at 9:30 AM on January 17, 2017

I think my response came across as snarky. My apologies, I didn't mean to be dismissive of your question.
posted by scottatdrake at 10:16 AM on January 17, 2017 [3 favorites]

It did a little, yeah. And now I'm wondering if that is why no one else is answering, or if there seriously is almost no one considered legit or worthwhile on the topic.

I appreciate the apology though. :)
posted by Serene Empress Dork at 10:20 AM on January 17, 2017

I get dozens of emails by choice daily, from Ramit Sethi to folks who want to teach you to make your own online course.

A decade and two ago, it was "buy this cd on eBay" and you get a how to on import and drop ship or turning around your own cds doing the same thing. Today its content creation with a dual drive towards brand creation and selling a continuity product (advice, newsletter, supplements, etc) and or a series of classes and books. Alternatively, they are multi level marketing (mlm) scams or junior venture (you sell something and get a percentage) or other venture with a high buy in for you or recurring costs locked into the privilege to resell the product or service.

This seems like a sensible start
posted by tilde at 10:34 AM on January 17, 2017 [4 favorites]

Patrick McKenzie's blog might be interesting to you. He's started (and sold) and few different businesses that have monthly income. He's pretty open about the numbers and process - the microISV articles might be a good starting point.

(ISV stands for "independent software vendor", and wouldn't be a terrible keyword for you to use as you look for information.)
posted by Nonsteroidal Anti-Inflammatory Drug at 10:40 AM on January 17, 2017 [3 favorites]

You should read Jen Dziura's website Get Bullish. I do not have an entrepreneurial bone in my body, but she's got a lot of great practical, feminist advice. I especially like the article on how she started a high-end cat-sitting service, as just a random example of how to find a market and build a business.
posted by gideonfrog at 11:13 AM on January 17, 2017 [8 favorites]

I used to get Ramit Sethi's emails, and while I never actually took any action, they seemed legit.

There's a book called the $100 Startup that made sense to me, although, again, I haven't actually done anything yet.
posted by kevinbelt at 11:18 AM on January 17, 2017

Hi! I'm an entrepreneur and business strategy consultant. I've started 9 companies on my own and I work with people every day who are starting or expanding their businesses.

I've read and listened to so many of these online gurus, trust me when I say it's all the same basic principles dressed up in slightly different language. You won't be missing anything major by choosing one over the other, I promise. Good ideas, building an effective website, marketing, networking, etc. The formula doesn't change. Different industries will have a slightly more specific 'how to get started' but once you've established that, everything else is pretty similar across the board.

The hands-down BEST resource I've seen for creating a successful business is the book Value Proposition Design. I cannot overstate how crucial the principles in this book are. It's something that is frequently left out of the 'guru-model', and I have all of my clients work through both it and its companion book, Business Model Generation.

Mostly what success requires is work. Lots of it. You won't be working 9-5: you'll be working a lot more. For years. If you are successful, you get to reap the rewards later.

If you don't have solid graphic design skills, learn them. It's a huge time and money saver if you can create your own graphics. If you can do your own web development too, that's even better. If you're promoting your business partially or primarily online, these are skills you can't afford not to have.

Good luck! Starting your own business is awesome and terrible in equal measure, but the rewards are worth it :)
posted by ananci at 11:22 AM on January 17, 2017 [21 favorites]

I really liked the 4-hour work week by Tim Ferris. I think it is a good overview of a lot of tools and strategies to help people who do not want to work 9 to 5. But I have not implemented those and do not make any claims about its effectiveness. It was a New York Times bestseller but I'm on my phone and can't link easily. He also has an online blog and consistently interesting ideas at least to me.
posted by Bella Donna at 11:54 AM on January 17, 2017 [1 favorite]

Patrick McKenzie's last business failed in a mere 18 months. He has returned to getting a paycheck from another company. It is likely a remote job.

Everyone says he is THE expert, but I do not actually ever run into anyone saying "I read his stuff and now I have a successful micro ISV!" What I do hear is "I read his stuff and went from making $100 an hour as an IT consultant to making serious money."

Additionally, a big way that he gets "press" is by being the number two ranked guy on Hacker News. There are currently zero women on the leaderboard of Hacker News. If you are a woman and/or not a programmer, his writing may not be the bee's knees for your purposes.

If you are a male programmer looking to be a well paid consultant, he seems to have useful things to say. Otherwise, my impression is he is more hype than real value.

posted by Michele in California at 2:16 PM on January 17, 2017 [2 favorites]

Here's another view of Tim Ferris. - #4 is the most relevant.
posted by warriorqueen at 2:47 PM on January 17, 2017 [2 favorites]

Additionally, a big way that he gets "press" is by being the number two ranked guy on Hacker News.

Yeah, that's a good point. That's certainly where I know him from, so...

Anyway the published numbers, which I couldn't find earlier, are probably what get a lot of people excited. It's all very "one weird trick" if you ignore the work actually involved.
posted by Nonsteroidal Anti-Inflammatory Drug at 2:54 PM on January 17, 2017 [2 favorites]

I work 9 to 5, but I was able to join a local club for freelancers/business owners (with its own mailing list, meetups, Facebook group, etc.). The main thing I've learned is that it's incredibly hard work to not work 9 to 5. Virtually everyone who's successful at it is already pretty successful in their chosen field (mostly tech) and could easily get any day job they wanted, and has invested years of 60 hour weeks working for peanuts to build out their business. One guy's ISV is finally doing pretty well, after making nothing for over 10 years! Don't get me wrong, working for yourself sounds pretty sweet, but it's not an easy path. I'd suggest finding a similar group in your own area.

Other ideas: follow the Mr. Money Mustache approach of working really really hard for a few years, saving up a ton of money, and living cheaply off investment proceeds. Work for a contracting company on 6-12 month contracts. Or just work remotely for an established company.
posted by miyabo at 4:04 PM on January 17, 2017 [3 favorites]

If I was going to abandon the 9 to 5 I would read everything Jon Acuff writes. I follow him on Facebook and his videos alone are really helpful -- and I have a regular job. Plus he's funny. Here are his books:
posted by LilBit at 8:29 PM on January 17, 2017

Having independence in your schedule is a benefit. And to get that benefit, you've gotta trade something for it; whether that's accepting lower pay, or accepting unsteady paychecks, or adding in a lot of risk that something might not work out (and possibly all three!)... if someone's selling a strategy that doesn't include tradeoffs, I'd be pretty skeptical, because otherwise we'd all be chasing that gravy train.

Mr Money Mustache is mentioned above. He's half spot-on and half hard to take seriously because of the tone and smugness. That said, his strategy is pretty simple; spend a lot less. Save a lot more. Retire much sooner than you would otherwise.

Example: Move to a smaller town that has enough work for you, but a much lower cost of living. Live in a house or apartment - whichever's cheapest longterm! - that's smaller than what you're used to, because it isn't making you happy enough to justify that cost. Sell your car, and bicycle everywhere. And take decent vacations, because our brains are wired up to love great experiences much more than they care about owning most things.

Do that for 20+ years, saving all of the money you would have spent in interest-bearing investments. Alternatively, do that for 10+ years, and then only take jobs that you'd do for free, which is what Mr Money Mustache refers to as "retirement".

It ain't a bad plan, but it does cost you pretty much everything.
posted by talldean at 9:07 PM on January 18, 2017

Aghh, I sort of hate recommending this book because it is half libertarian/ugly political views and also the name is terrible and sounds like get rich quick nonsense, and yet the business side of it is fairly true:

The Millionaire Fastlane

It really probably isn't for everyone, and like I said I kind of hate recommending it, so only check it out if you can extract the good information out of something while ignoring the nonsense (and there is nonsense).

There are a lot of different business models and ways to make money online, but the three sites I like the most, when it comes to business ideas and website building:

Viperchill and Gaps (same person so I count this as one)
Authority Hacker

I have made a living online since 2002 web publishing, have employees and a small company etc., for whatever it is worth. The flexibility is great, but I have probably worked more hours than anyone I know over that time, so there's good and bad.
posted by imabanana at 4:47 AM on January 19, 2017 [1 favorite]

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