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You’ve seen the Facebook ads promising that “you too can have your own business making six-figures from your couch while wearing yoga pants — or no pants! Just download this quick guide, and you’re on your way.”

And you can’t miss the countless Instagram accounts of burgeoning entrepreneurs who (at least according to their carefully curated social media feed) seem to constantly be working poolside, traveling the world with just their laptop, and generally living it up now that they’re self-employed.

Maybe you’ve even read The 4-Hour Work Week, or another one of the countless entrepreneurial books that have hit the bestseller list in recent years, promising huge payoffs and tons of freedom in exchange for just a few hours a week of running your “lifestyle business” online.

In case you’re not familiar with the term “lifestyle business,” it’s a popular way of describing a business you create with the primary intention of it supporting your ideal lifestyle. Usually that means having location independence, total creative freedom, schedule flexibility, and unlimited income potential.

Sounds amazing, right?

People want more flexibility and autonomy in their career than ever before, so a lot of us find the idea of a lifestyle business especially alluring.

I’m sure you’re sensing a “but” coming, and you’re right. Well, more like a yield sign. Because I’m obviously a big fan of lifestyle businesses! I’m the freaking co-owner of one.

And it’s actually because I’m so intimately familiar with the inner-workings of this type of entrepreneurship that I want to make it super clear what it’s REALLY like behind-the-scenes.

That way, if you’re considering starting your own lifestyle business — or if you’re feeling tempted by those perfectly posed Instagram posts of laptops in exotic locations — you’ll have a real picture of what it’s like so you can make the right decision for you.


Let me first assure you that I love my business, and I wouldn’t trade it for any other career in the world (although you could tempt me with a job at Black Jaguar-White Tiger, one of Rachel’s and my Instagram obsessions).

There are a LOT of perks to having a lifestyle business:


But running a lifestyle business is not all a freakin’ walk in the park, let me assure you.

There are more than a few “shit sandwiches” that come along with it … things you’re not likely to see on social media or hear many “lifestyle entrepreneurs” talking openly about.

Things like:


Here are a few big things to consider before deciding if you really do want to work for yourself:

Consider your values. How strong is your value of stability compared to your desire for autonomy and freedom? What’s your risk-tolerance? (Pssst, your Passion Profile will help you identify your values, especially when it comes to HOW you should be working.)

Are you willing to eat the “shit sandwiches”? Sure, the perks of working for yourself are pretty fantastic. But you’ve got to be willing to put up with the downsides that come along with them. What’s your level of willingness?

Explore all of your options before diving headfirst into entrepreneurship. Is there another way you could be just as happy and get some of the same perks of self-employment without full-out quitting and working for yourself? For example…

I’ve heard entrepreneurship described as “living a few years of your life like most people won’t, so that you can spend the rest of your life like most people can’t,” and that’s pretty much spot-on.

The question to ask yourself is … does that excite you or turn you off?

Tell me, have you considered working for yourself? How do you feel after seeing this behind-the-scenes perspective? Or, if you already do work for yourself, do you have more to add to my lists of pros/cons? Share with me, in the comments below!

Much Love,

Kristen (& Rachel)


Ghosting your job with Lana Jackson (May 2018)

Blog: How to transform what you don’t want into what you do want (August 2018)

Blog: Why you should keep new ideas to yourself (December 2018)

Side Chat: The 4 Passion Profiles (December 2018)


Take the Passion Profile Quiz

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  1. This is awesome! So many people are into the whole lifestyle business idea without really understanding how much work it actually is. This is a great post for anyone who’s considering it. (As you know Kristen, the definition you use here for entrepreneurship excites me, lol, but it is crucial to understand both sides of the equation. Great post ladies! I’ll definitely be sharing! <3 Amber

    1. Hey Amber! I had a feeling this description would be more exciting to you than off-putting. 😉 I figure it’s helpful for anyone, regardless of their level of interest in self-employment, to have the whole picture before deciding if it’s right for them. Glad you enjoyed this behind-the-scenes view. And thanks for sharing this post!

  2. OMG this could not be more spot on! (Rachel, you know how much I identify with all of this) Thank you ladies for writing this so I can share with anyone who asks me what starting my own business is like/if they should start their own too 🙂

    1. Hi Carolyn! Glad to hear it’s not just Rachel and me struggling with some of these challenges of self-employment! Although, in the end it’s totally worth it, right?? I just wish I’d known the WHOLE story before diving in headfirst — so, I thought I’d give everyone else the insider insight I wish I’d had several years ago! Thanks for sharing! 🙂

  3. Really keen on quitting my job and just doing my own thing, problem is what? A lot of people say you need a plan, or need to start working on something while you have a job. It just feels that a job consumes me and my thinking and the time I then have for myself I dont want to work more or do brainstorming when I just want to chill. Hmmm confused.

    1. I totally understand this catch-22, Jana! While I agree that it’s a good idea to start working on your business while getting at least some income from another job (since your business likely won’t provide for you financially, at least steadily, for a couple of years), it sounds like your current job might be too draining to support your business vision. You may want to consider getting a bridge job that gives you more time and/or energy to work on your business, while still paying the bills.

  4. You nailed it Kristen! I love your (and Rachel too) honesty. Entrepreneurship is humbling, uncertain, and scary. And for many of us, that never stops! Love you guys! XXOO

    1. Hey Lauren! 🙂 It is SO humbling — you’re totally right about that. I feel suspicious of any entrepreneur who claims to be completely certain and fearless about what they’re doing. Uncertainty and fear are part of the deal!

  5. Kristen (and Rachel), you guys did a really great job with this post. A lot of people just think about the glamorous side and don’t think much about how there could be months of “Holy shit, no one’s going to hire me ever again!” It’s a lot of hard work. Definitely a labor of love.

    1. Thanks, Cindy! 🙂 Yeah, it’s definitely not all fun and glamour all the time! It’s way more work and uncertainty than it often appears from the outside. This post could have also been titled “What I wish I’d known before diving headfirst into working for myself” lol.

  6. Great post and timing couldn’t be better for my current situation…but brings up more questions 🙂 How do you guys feel about a lifestyle business and a Thriver passion profile? I couldn’t be more of a Thriver but did a lifestyle business for 3 yrs (real estate agent). Loved having ownership in something and also experienced every point (good and bad) in the post! In the end the income instability scared me enough to go back to corporate for last year…money is great but HATING IT! Questioning if being a Thriver is a detriment to having a lifestyle business? Thanks!

    1. Hey Brian — Such a great question! I’m part-Thriver myself, so I’m very sympathetic to the desire for a lifestyle business, but also the fear of income instability and too much responsibility. You’re not alone in fighting that internal tug-of-war!

      I definitely think lifestyle businesses can work for Thrivers, but I think the structure might need to be a bit different from the real estate business you experienced. This isn’t a rule or anything, but in general I think Thrivers would be better suited to lifestyle businesses that focus on creating passive or residual income, which would provide a bit more reliability. Also, Thrivers might like having a part-time gig that they can simply clock in and out of (or that they can do remotely on their own time), that’s super low stress and that provides some steady income while they’re building their business.

      Thoughts? Does any of that resonate with you?

  7. Hi Kristen – thanks for taking the time to respond. I completely agree with you on the lifestyle business being THE only income source for a Thriver. I couldn’t stand when I was trying to have fun with friends (golf/hockey/hanging out) or having family time and people were calling at all hours of day/night. I think your suggestion of passive or residual income satisfying the lifestyle business urge is on point. My only problem or question for the full time stable “9-5” gig is I’m at a point in life (41 yrs old, married, 2 kids, decent size house in the burbs) where I’m making a great income. The expectations that come with that are more “7-7” with nights and weekends. I feel like I need a magic fairy to grant me a wish for a job that’s truly 8-5 and I can leave work at work while making enough to keep family relatively comfortable and fund my hobbies. I’m in the middle of the PPSC and coming to some great conclusions about what I want/don’t want. I can envision my perfect life but just seems more dream than reality with the “jobs” that are out there for my background/skill set. Thanks again for the feedback and love your site!

    1. Hey Brian — Glad that feedback on lifestyle businesses for Thrivers was helpful! I 100% understand that real-world obligations and responsibilities HAVE to be a consideration when you’re considering the next career step. I know it might feel like your dream career is a pie-in-the-sky vision, but I want to challenge your belief that all well-paying jobs require you to work 12-hour days (or longer). (You’re probably already challenging some of those beliefs in the PPSC!) Can you find examples of people making a good living for themselves while working more normal hours? It’s hard to make a change — or even seek out a change — if you don’t believe it’s even possible. So it might help to first find some proof that what you’re looking for exists out in the world, and then you can start to believe it might be possible for you. I hope that continuing with the PPSC will help you get clearer and clearer about what you’re looking for!

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