How to tell if you should quit your job and work for yourself

work for yourself

Click the play button below, or subscribe and listen through our podcast on iTunes, Stitcher, Google Play, or Spotify.

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 the newly 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?

It’s no wonder so many people are attracted to this concept right now. Millennials, in particular, seem to want more flexibility and autonomy in their career than previous generations, so a lot of us find the idea of a lifestyle business especially alluring.

But no matter who you are, this is tempting.

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 photos 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:

  • I’m fully in charge of my own schedule. Which means I can take a random Wednesday off just because I want to, go to yoga in the middle of the day, or have a 2-hour lunch with a friend without checking the time … and never have to worry about how many vacation or sick hours I have left.
  • I get to make the impact I most want to make. I’ve worked for companies that had respectable missions that I genuinely cared about (along with a few that I never cared about), but it wasn’t nearly as fulfilling as doing the work I most want to do in the world: helping people become more self-aware and really know themselves on a deep level so they can create a life and career that perfectly suits them.
  • I have total creative freedom over my work. Everything about Clarity on Fire — from the design choices to the programs we offer to each individual blog post — is 100% representative of who we are and what we stand for. I never have to pretend to care about something I don’t, or hold back my opinions, or in any way alter who I am in order to “succeed” in my career.
  • I work with amazingly cool people. Not only do I get to work with my best friend of over 10 years, but my clients (and our program participants) are incredible people, too. Which makes sense, if you think about it — if I’m “promoting myself” by simply being myself, I’m going to attract people who resonate with me, and we’re bound to get along swimmingly.
  • I have unlimited income potential. Unlike a traditional job where I’d have a set salary and have to ask for a raise if I wanted to make more, owning my own business means there’s no cap on how much I can earn. So I get paid according to how much effort I put in, not how many hours I clock.


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:

  • Income instability — often for YEARS. Some months you might rake in the dough, and other months you’ll watch your bank account balance drop without knowing exactly how you’re going to replace it.
  • Never knowing if you’re “doing it right.” Since no one’s telling you what to do to build and grow your business, you’re never totally sure you’re doing the “right” or “best” things. You constantly feeling like you’re throwing spaghetti against the wall to see what sticks, which can be seriously frustrating.
  • A TON of responsibility — for your own financial wellbeing, for your customers/clients’ needs, for the future of your business, etc. The weight of the responsibility can be heavy at times.
  • Never being able to totally disconnect from your business. I always have to take my laptop on vacation just in case someone has an immediate question or needs technical help. Sure, you could hire a team, but that requires paying and managing a team, which gets into even more responsibility.
  • Essentially having two jobs. You have to be equal parts a business owner AND an expert in the product/service you offer, which are really two totally different jobs.
  • Sales. Need I say more?
  • Being fully accountable to yourself. Being your own boss means you’re 100% in charge of managing your time, energy, and priority list. It also means you have to hold yourself accountable — procrastination only hurts YOU when it’s your business.
  • No guarantee of success. There’s no magic formula that, if you follow it, guarantees you’ll be successful in business. You’ll likely spend years pouring yourself into your business with no proof that it’s going to pay off.
  • Feeling like a slob because you haven’t put on real clothes in Or brushed your hair. Or put on makeup. Or gone outside except to get the mail.
  • Loneliness & isolation. Running a business can be lonely. This is less of an issue for me than it would be for a solopreneur, since I have a business partner. But even Rachel and I feel isolated sometimes. Not only are you working alone a LOT, but it can feel isolating to be doing something somewhat unconventional, especially if you don’t have entrepreneurial friends/family to talk to about it.


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…

  • Remote work. If you really value flexibility, then working remotely for someone else might scratch that itch with WAY less responsibility and unpredictability.
  • Intrapreneurship. If you really value leadership, then being an “Intrapreneur” — someone who champions an idea or spearheads a mission within a company — might be perfect for you (and way less lonely).
  • Commission-based work. If you really value unlimited income potential, but don’t want to be in charge of the whole business, you might thrive in a commission-based environment where you’re paid more for your effort than your time.
  • Side business/project. If you really value creativity and autonomy, then you could pursue a side business or project to express yourself, help others, and create something that’s all your own, without the pressure of needing it to fully replace your income.

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

Submit your question for a future episode of Dear Krachel

Check out our YouTube channel

14 Comments // ADD COMMENT


  • Amber Duffney

    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

    • Kristen Walker

      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!

  • Carolyn Birsky

    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 🙂

    • Kristen Walker

      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! 🙂

  • Jana

    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.

    • Kristen Walker

      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.

  • Lauren Mowbray

    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

    • Kristen Walker

      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!

  • Cindy

    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.

    • Kristen Walker

      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.

  • Brian

    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!

    • Kristen Walker

      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?

  • Brian

    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!

    • Kristen Walker

      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!