Corbett Barr

Lifestyle Business Weekly

Starting a Business Isn’t All Unicorns and Rainbows (the Other Side of the Story)

A reader emailed me this week with a suggestion.

She left her job over a year ago to travel the world and start a business with her partner. After struggling to get her business off the ground for the better part of a year, anxiety got to her.

Despite having significant savings, she became so distracted by money-related fears that she could no longer focus on building the business.

She started look for a job.

She found a great job. Excellent pay, fantastic benefits, flexibility on travel. The ability to live a great lifestyle without being self-employed.

So what’s the problem?

As I was reading this story, I couldn’t help but think about how familiar it sounded to my own story.

I too left a comfortable job to start a business. I too started feeling anxious about living off my modest and hard-earned savings.

My anxiety got so bad I sought medical attention. Stress can be debilitating for entrepreneurs. For some reason I slogged on, despite having no income, no investors and dwindling personal funds for a year. Twice.

I also came very close to looking for a job, and my path could have been very different if I had.

This reader wrote in to suggest that I offer some perspective on the issues and questions both she and I faced when starting a business.

So here it is, the other side of the story.

Yes my ambitious friends, starting a business isn’t all unicorns and rainbows. It’s always challenging and sometimes scary as hell. Brace yourself.

As this reader pointed out, the rhetoric around lifestyle businesses is usually one-dimensional. I know that I too often sound one-sided on the issue.

The truth is, starting a business is hard. It’s definitely not for everybody.

Regarding our reader friend who started this discussion, I’m not saying starting a business isn’t for her. She could still very well end up becoming self employed in the years to follow. Taking a job isn’t any sort of defeat. It’s simply what you might be right for you at the time.

Let me clear up a few things before we continue. I’ve written many times about my views on self employment. I’ve often been harsh on jobs in general.

I wish there were far more self employed people and small businesses in the world. Our economy and society would be better off with fewer big corporations. Concentrated wealth and power corrupts. People are often happier and more fulfilled when working for themselves.

BUT, that doesn’t mean people who work jobs are losers or weak or uninformed or flawed in any way. Many of my closest friends work “regular” jobs.

Some people choose to work a job because they love what they do. Some people choose employment over self-employment because it’s comfortable or lucrative or challenging in a different way.

Some people simply know that they wouldn’t make good entrepreneurs.

Other people work jobs because they haven’t figured out what they really want to do with their lives.

In any case, there is nothing wrong with having a job. If you currently have a job, there is no reason to feel bad about that.

Don’t let anyone who runs a business or even a “lifestyle business” tell you how to feel about what you do for a living.

It’s up to you to decide.

When I write about my love for self employment and the lifestyle I live now, I’m sharing my personal feelings, and I’m talking to a certain group of people.

If what I say resonates with you, great. If not, that’s fine as well.

I don’t think I’m special or superior because I’m an entrepreneur. In fact, sometimes I think entrepreneurship is an affliction.

Everyone is different, and I’m not suggesting that everyone should be self-employed. On the contrary. That’s why I also occasionally write about what employers should do to be better bosses.

There are some fantastic and important jobs out there for smart and ambitious people. There are employers who care about their employees and what they’re contributing to the world.

Unfortunately there aren’t enough of these caring, sharing employers. The facts say most people are unhappy with their jobs.

I knew that I would never be satisfied unless I gave self employment a real shot. I even had a very flexible job, with incredible benefits and unlimited time off. Still it wasn’t enough for me.

I know a lot of you feel the same way, and that’s why I write so passionately about entrepreneurship.

The Other Side of the Story

As you’ve probably noticed, the blogosphere is full of people who like to tout the benefits of self employment without talking about the other side of the story. Again, I’m sometimes part of that group.

Self employment can be an incredible way to live. It has made me happier and more fulfilled than anything else I’ve achieved.

But the other side of the story is something every would-be entrepreneur or lifestyle business builder should consider.

These facts are very real, serious, and not to be overlooked:

  1. Starting a business while traveling at the same time is damn near impossible.
  2. Quit your job! Start a business! Travel the world!

    Maybe you’ve read similar rallying cries online recently.

    If only it were that easy.

    The truth is, it’s damn near impossible to get a new business off the ground while traveling. Sure, you can travel once your business is stable, but building a business takes serious dedicated, concentrated effort.

    Backpacking around Southeast Asia might be fun, but don’t expect to get much real work done. In fact, you’ll probably just be frustrated by your inability to truly enjoy either the traveling or the business building.

    I built my business partly while living in Mexico, but most of the effort I’ve put in happened while I was stationary for months at a time.

  3. Personal problems don’t disappear just because you’re self employed.
  4. If you’re seriously unhappy, don’t look to self-employment as a cure-all. If anything, your natural psychology will become amplified during the startup phase of your business (which usually lasts a few years, by the way).

    Starting a business is an emotional roller coaster. If you don’t have a strong emotional foundation, that roller coaster might make you crazy.

  5. Serious anxiety and even panic disorder are very common among new entrepreneurs.
  6. I mentioned earlier that my anxiety became so severe that I talked to a doctor about it. It turned out my startup experience had brought on a case of panic disorder.

    Eventually I learned to deal with the stress and the condition went away. While I had it, I made some ridiculous decisions and had a hard time getting any serious work done. It’s hard to say how much that level of stress damaged my health long-term.

    Most entrepreneurs I’ve talked to go through something similar, do differing degrees. For some it’s bad enough to kill their business plans altogether.

  7. Your relationships may suffer because of your business.
  8. Can your close personal relationships endure month after month of you being physically unavailable or emotionally distant?

    My wife is incredibly supportive. I’m very lucky that’s the case, considering how many years I’ve spent in the grueling “startup” phase of businesses.

    If your spouse or family isn’t so supportive, you have to decide if the risk of damaging your relationships is worth it.

  9. There’s a very real chance your first business attempt won’t succeed.
  10. You need to be able to accept that. If you can’t live with that possibility, you should probably do something else.

    I failed twice before I succeeded. I knew about the risks and accepted them. My goal was to learn from each failure and I didn’t count on any one business as being the perfect opportunity.

    Maybe you’ll fare better, and maybe you won’t. If you do accept the possibility of failure, I suggest you focus on winning the war (building a business) and not on winning every battle (any specific project or business may fail).

For me, these harsh truths weren’t enough to keep me from building a business that supports me and that I’m incredibly proud of.

I live a charmed life because I fought for it.

For you, the answer might be different. Hopefully this honest look at the other side of self employment will help.

If you read this and are still committed to building your business, welcome to the club. You have entrepreneurship in your blood.

Has your experience with self employment been similar? As I said, everyone is different. This is just my perspective.

I’d love to hear your perspective in the comments below.

And if this article helped you, I’d love you to share it with someone who could also use it. Just click the sharing buttons below.

The reader who started this discussion with me over email is Leah Neaderthal, and her business is called Start Somewhere. They help companies who “do good” to create compelling websites, logos and marketing.

Leah’s partner Leanne Pittsford is taking the next steps to grow the business, bringing additional people on board, and focusing on business development so that in a year they can re-assess and Leah can join the business again.

Thanks Leah for the inspiration for this post and good luck to you and Leanne with the business. Let us know how things progress.

Corbett Barr

A weekly curated email of useful links for people interested in lifestyle businesses and independent entrepreneurship.


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Let It Go.


  1. Definitely think point No. 5, that the first business likely won’t succeed, needs to be underscored. The person with entrepreneurship in his/her blood won’t give up easily, but it is important to be able to fail quickly.

    • Corbett

      Yeah, it’s hard to watch when an entrepreneur clings to one particular idea even after it’s pretty clearly a failure. There’s no need to go down with the ship if something isn’t working.

  2. Oh, the anxiety! Oh, the fits + starts!

    Yes. It’s not for everybody, and when your savings dwindles down to your last dollar it’s pretty much do or die time, which is exactly where I am. Which is how I’m starting 2012 – with a renewed sense of commitment to personal and financial freedom. THIS IS THE YEAR! I’m relaunching my site very soon, getting my book out there in a few months, and nestling deep down into WHY being an entrepreneur is essential for me. There’s no other option, truly. But I know not everyone feels that way.

    Thank you for talking about the shadow side. Because sometimes people think if it’s not out on the table, then it’s not really there at all – and there’s enough denial of the dark + difficult already in our society which only makes it pop up in inconvenient ways.

    Happy New Year, Corbett!

    • Corbett

      I like the attitude Kellie! Here’s to a tremendous 2012 for you and your business plans. Thanks for sharing and let us know how it goes.

  3. Great point of view. Your words are so truth. Thanks for it.

  4. Corbett, this is one of the best posts that I’ve read in a long time. I was nodding my head reading through the whole thing, and couldn’t agree more – I wish more people understood just how much work goes into building something real. Thanks for this! :)

    • Corbett

      Awesome Danny, I appreciate that coming from you, especially with both the success and struggles you’ve gone through recently.

    • Great summary: “Wish more people understood just how much work goes into building something real.”


      And Danny, I’m surprised you didn’t mention your recent entrepreneurial failure post over at Firepole Marketing… would it not be appropriate / relevant / helpful?

  5. I’ve heard a number of folk who work with business owners for business-related stuff issue variants on the theme of “this client of mine doesn’t need business coaching. He needs therapy.”

    I’ve thought the same about a couple of folk I’ve worked with.

    It’s a vicious circle, too. The more miserable you are, the less likely you will be give it all to whatever it is that’s making you money. Thus you’ll do less well. Thus you’ll be more miserable.

    Most people are better off employed. Most people are better off working in a team. That’s not a bad thing.

    I’m fucking miserable sometimes. I am DAILY tempted to take a paycheck. And I will, one day, if that’s the right thing to do. At the moment, happily, it’s not.

    No shame at all in pulling pints of beer. Those guys keep me alive ;-)

    • Corbett

      Thank god there’s always beer :)

      And yeah, entrepreneurs could definitely benefit from therapy as much or more than business advice most of the time.

  6. Three years ago, I worked in the arts as a freelance technician, lighting designer and stage manager. People would often wonder how I could bounce between two and three theaters in a day, sometimes in different states, work long hours and occasionally spend an overnight in front of a light board. While I can’t say those moments were fun, my answer was always the same. I can’t *not* do it. It was in my blood, so to speak, and I couldn’t imagine having a “regular” job. After six years in the business, it started to wear thin, and I knew it was time for me to persue other things. I was able to envision a life outside the theatre, and so I opted for one and took a 9-5. Now I have the entrepreneurial bug, and I’m laughing because I know exactly what I’m in for and I can’t wait.

    So I agree with you that we all have to make our own choices, and neither choice is wrong or bad. In fact, if we get out of the mindset that whatever we choose now has to be our answer forever, then it takes some of the pressure off too. I’m not recommending dabbling in entrepreneurialism and running back to a job the minute it gets hard, but many people have gone on to build successful businesses, sell them and take jobs. Things change. We are not solely defined by our work, and it’s okay to make different decisions at different times in our lives.

    Way to go, Leah and Corbett, for the honesty and insight!

    • Corbett

      Well said, Sarah! Entrepreneurship is like a lot of difficult things in life. You can come to relish the challenge and uncertainty of it all. It’s part of the journey and part of why we do it. As long as you’re willing to roll with the punches it all becomes exhilarating.

  7. You summarize everything here Corbett. It’s almost two years now that I am trying to win the war. I learned a lot from my two first blogs but I must admit that they didn’t succeeded in bringing me yet the style of life I am fighting for. I am not giving up. I am learning learning… and finally learning mainly from these two previous failure.
    It’s really not that easy … Even if I read one time a guy :) telling me that with ” 18 months, 2 blogs … you can earn a 6 figures income :)
    With your point 1, I can only attest that this is completely true. I would have like the contrary but it’s almost impossible.
    Point 2 and 3 are not really my problems : Pretty sure that meditation is for something here.
    Sadly, I must admit that I recently was touched by your point Number 4. I always thought my husband was very supportive of my attempt to make this business, for me, for him, for us… Because it would support his desire to go back living in his native country Tunisia. But day after day, month after month being always fully implicated in my business, started to create some vileness to him. It was so surprising for me when I discover this… So sure here, I decided to take more care of him than of my blogs…
    So Corbett I 100% agree on all what you wrote here :) Thanks for this …

    • Corbett

      Hey Daphné, thanks for writing. Keep in mind when I wrote about my first 18 months with blogging, I had already spent years learning to be an entrepreneur. Always consider someone’s backstory and how it prepared him for whatever “overnight success” you might be reading about. Consider your own backstory. What about your past could help you with your current pursuit? There may be things you’ve overlooked.

  8. My experience has been similar, and I’m just a the beginning! I’m planning to leave Toronto next year and travel around the US on a climbing trip. Im already gearing up for this to be extremely challenging, and I’ve made it clear to my partner that I will be setting a regular work schedule and that he’ll have to find a new climbing buddy on those days.. We’ll see how it goes! :)

    • Corbett

      Congrats on setting the expectations ahead of time. That can do a lot to free you up for what you need to do.

      Have a great time on the trip. Remember to enjoy the adventure while you’re on it. Work will always be there when you get back as well.

  9. Great post, Corbett! Thanks for sharing this perspective. You’re right, much of what you read “out there” tends to be very one-sided.

    The pit in my stomach that I have been feeling lately while contemplating all of these things that you discuss came back while I was reading. I’ve found that it helps me to deeply consider the “why” I want to go down this path and then work from there. It puts things in perspective for me.

    I have a feeling I’ll be re-reading this post a few more times in the coming months. Thanks for writing!

    • Corbett

      Hey Rick, thanks for sharing part of your solution for dealing with all this. I’m sure I’ll be covering the coping mechanisms I used in future posts as well.

  10. Thanks for this. Really appreciate something that’s brutally honest as it helps people to see both sides. It’s what we always almost missed out when taking on self-employment.

  11. Sol Soloncha

    Thanks for this post Corbett. There is a lot to be admired and aspired to in starting one’s own business and not working for someone else—it’s a beautiful and important ideal. However as you mention, the majority of writing in the blogosphere promoting entrepreneurship barely mentions the other side of the coin… This can be exuberant optimism for some, but it smacks of selling a belief in Santa Claus sometimes too. I prefer those writers on entrepreneurship who include mentioning the potential for adversity when discussing how one actually might make something happen with one’s own business venture.

    I like your blog. Thanks for another good post.

  12. Excellent post. Currently going through a similar situation. I left my job and started to work on my passion. I had the same panics on daily and almost called my manager several times to get my job back but something inside is always telling this what you are supposed. It’s very tough and you have stay strong when you don’t know when if you are going to make enough money to cover your monthly expenses.

    Thank you Corbett for this post and thanks to everyone for shared their views and stories.

  13. This is a great one, Corbett.

    Over my 8+ years in the Army, the majority of it was okay with me. Sure, I didn’t like spending a year at a time in Iraq or Korea but it’s something that we learn to deal with as Soldiers.

    On the side, because I learned things that would never allow me to be the same again, I would attempt to be an entrepreneur. Either my work with the Army or my internet business would struggle, and I would always end up easing back online. I hated that.

    I had a good paycheck, though, so it wasn’t a huge deal.

    However, about 7 years into my career, and about 4 years total of soaking up information that made me want to chase my dreams, I started to become a different person. Now, I was in the Army surrounded by people who didn’t mind the mediocre lifestyle and they were content with just complaining about it but still doing it.

    That ate me up inside. So, I attempted to help the people around me grow in the way that I had been growing. Long story short, I ended up in the hospital with anxiety issues stemming from having such high expectations of people that would never be met.

    They thought I expected too much. Is it true? Well, maybe for the military environment, but not for a group of entrepreneurs.

    I say all this to point out the fact that some people just can’t hack it in the job market… from regular employee to Soldier. I couldn’t. I need to see the people around me aim for higher and only chase their dreams. For the most part, most people don’t have dreams of working an average or even slightly above average job.

    So the normal job path is what actually sent me to the hospital.

    As you know, Corbett, I recently left the Army and now I communicate with entrepreneurs more than Soldiers or anyone else with a regular job. And I must say, my only anxiety is the good kind.

    Different strokes for different folks. The key is to just be real with yourself…

    Wonderful article.

    • David Robinson

      Hey Sean,
      A few of the things you said resonated with me. I was in the British Army for 10 years and I was probably one of the people complaining about the situation but not doing anything about it. Looking back, I think the military can be quite a constricting environment, you’re put in to your ‘slot’ and because of the time away you don’t interact with enough types of people. While doing some amazing things, learning great skills, your experiences are limited to the military environment.

      This caused me to feel dissatisfied and after being out for nearly 2 years I feel I have grown a lot as a person. Although I’m still not sure what I want I have relished the new experiences and have a stronger desire to learn than ever, I also feel I have some of the entrepreneurial bug, or “affliction”!

  14. Thank you! I just started my own business after freelancing for 2 years and agree with ALL of this. It’s not easy – sometimes, it downright SUCKS. There’s still the stress of money, and everything in between but the difference, for me, is that it’s a good kind of stress. I still want to get out of bed in the morning, even if I know that a hard day is waiting for me (versus my previous jobs when I was too depressed to even go in on certain days).

    These are points that also need to be shared with friends and family who think that, just because I’m self-employed, things are peachy and I’m not allowed to have bad days because “I’m living the dream.”

    I’ve also looked for jobs, and considered that but now that I have my client, and projects are starting to come together, I’m glad I made the decision to stick it out.

    Again, thank you SO much for this post. It was exactly what I needed to read this morning.

    • Corbett

      Great points Berrak.

      The difference for me is also that the motivation to do what I need to do comes naturally. That was never true when I worked a job. I always seemed to have to dig deep to find the energy to get work done. Now it just happens and I love every minute.

  15. just started my own company as well while still being employed. This is definitelly not “All Unicorns and Rainbows”. i.e. sleep only 3-4 hours a day. But would I go back? Hell NO! Only forward and eventually will be able to quit my job completely :)

  16. This is one of those rare posts saying it as it really is. I have written a similar post sometime ago too, I called it the “dark side of entrepreneurship”. I find posts like this very helpful as it put things in the right perspective for budding entrepreneurs. These days, the allure of successful entrepreneurs tend to be more celebrated than the journey of entrepreneurship itself. I think if more entrepreneurs begin to talk more about the journey than the outcome, they will see and realize ahead what they are getting into. This will help to remain focused and keep the anxiety level low.

    Thanks for sharing Corbett.

  17. Thanks for your post and pointing out the sometimes downsides of entrepreneurship. I never considered my ability to be self employed as a reality until the last few years, when I realized I am so miserable working for someone else that this really is the only option for me. I saw my negative beliefs about my ability to work for myself is what stood in my way of making the decision to quit my job and pursue photography full time.

    It has been a year now and I am happy to say I am getting by but know the stress all too well of not knowing what your income will be from month to month. I have been redesigning my website and making decisions of what to focus on to help grow my business. Some days feel so overwhelming because there is so much to learn, but I wouldn’t trade it for a full-time job in a million years.

    I enjoy reading your blog and look forward to future posts.

  18. One of my favorite posts from you. Very honest, but you didn’t scare me off.. I’m still trying to get my business going this year! I grew up around nothing but entrepreneurs.. I think I wanted to be self-employed when I was in kindergarten, lol. So, difficult or not, it’s just meant to be :)

    • Yeah, Denise, I love this post, big time, and went through everything in it. Thanks for sharing it.

      That’s the thing though, you could name any successful entrepreneur and they’ll most likely connect with this, because it’s just part of the territory.

      I feel we all go through our own versions, and we come out the other side better than ever.

      The entrepreneurs early years is kind of like a needle, it doesn’t have to hurt so much when you know it’s coming. (Or maybe at all if you’re really in the zone :D)

    • Corbett

      Thanks Denise, I’m glad I didn’t scare you off :) I’m the same way, I thought I’d be self employed when I “grew up” for as long as I can remember.

  19. Good writing ,and true words. I would say that if you’re during your first business attempts, you’re 99% likely to fail.

  20. Sam

    I appreciate your honesty Corbett. Entrepreneurship is difficult, but the harder it is, the more you respect yourself when you overcome each hurdle. I like the fact that it’s hard because it prompts personal growth in all kinds of ways.

    I recently quit my job and am building my internet biz from my bedroom at my parents house. To work on it full-time without having to be employed this year, I have a budget of 500US per month for EVERYTHING (because I only have a few thousand in savings).

    To say my personal life is having to suffer a little would be an understatement – yet I wouldn’t have it any other way. I’ve committed to this, so if this is what it takes, so be it.

    • Corbett

      That’s some serious bootstrapping Sam. Luckily it’s cheaper than ever to get a business off the ground.

  21. Hey Corbett! A much needed take on the whole thing. I’m getting ready to take on the leap and it’s quite awesome to read these kinds of stuff. It’s true that, as an outsider, you look into the lifestyle business’ blogosphere and you’re easily carried away by the illusion of easy success. I think it’s noble to want to share the other side of the story. At the end of the day it’s all about challenge and personal pride (as in, being proud of your achievements and your growth), but that cannot happen without proper acceptance, understanding and a little bit of anxiety, which if you’re wise, will only make you push even harder and make it happen. Great read!


  22. Yes, starting a business is hard.

    It usually takes more time and more money than the entrepreneur envisions.

    What continues to surprise me is the number of first-time entrepreneurs that I meet who believe that their experience will be different – all unicorns and rainbows!!

    I wonder if you enter into the situation with the understanding that it is going to be hard (emotionally, financially, socially, etc.), if the stress levels are any lower?

    As someone who works with entrepreneurs, sometimes I wish I had a therapist’s training!!

    • Corbett

      I definitely think a more complete understanding could help new entrepreneurs to experience less stress, although support groups and mentors are even more effective in my experience.

  23. Out of the park post, and somehow, even though practically everyone in the community knows you and references you, Corbett, this is my first time here. (Though I have commented on ThinkTraffic before! :D)

    Anyway… I, like many here, love this post, and I’ve written a few similar ones!

    It felt like a breath of fresh air, and an authentic look at what most (all?) entrepreneurs go through.

    I’d like to add my 2cents, and clarify — on a slightly larger scale — what is going on, with this whole “entrepreneurial journey” deal. It follows some key principles of character and personal choice.

    If you take any person, and any situation they engage in, it goes something like this (a general overview)…

    1. Every human being has a certain “habit of character” or “emotional setpoint”. (for any given topic)
    2. This helps them to handle certain situations smoothly, and some less-so.
    3. A person can choose to “play small” or “take on major life changes”.
    4. If a person chooses to play small, *chances are* they go through minimal adventure, and minimal self-discovery.
    5. If they choose to play big (entrepreneurship, a new relationship, marriage, moving to a new continent/culture, etc.), *chances are* they go through increased adventure, and increased self-discovery.

    So basically, any large undertaking in life will amplify Who You Are, What You Stand For, and your Emotional Strength/Discipline.

    Understand this, and be ready for it.

    If you have fantastic character + emotional strength, your undertakings will shine, whether they ‘appear hard’ to outside viewers or not.

    If you have mediocre character + emotional strength, your undertakings won’t shine, and will probably appear as ‘failures’ to outside viewers. BUT they will BUILD character and emotional strength, so you will be more ready if you were to go again.

    Alright, it was more than 2 cents…

    Thanks again for the food for thought and eye-opening post.

    • Corbett

      Hey Jason, welcome and thanks for leaving a great comment on your first visit.

      I especially liked what you said about building character and emotional strength. Some people succeed on their first outing partly because they have a great foundation of character. Others of us need time to mature. It’s all part of the fun and adventure in my book.


      • My pleasure man, great to be here :)

        And I think you summed it up nicely.

        Some of my favorite lines from your post:

        “In any case, there is nothing wrong with having a job. If you currently have a job, there is no reason to feel bad about that.”

        “If anything, your natural psychology will become amplified during the startup phase of your business (which usually lasts a few years, by the way).”

        “I live a charmed life because I fought for it.” – This last one is funny to me, because I generally prefer non-violent/non-fight metaphors, but everything has it’s place.

        The way the same idea would come out of my mouth would be:

        “I live a charmed life because I *took a stand and decided* that that’s my standard.”

  24. Amen amen! Being a lifestyle entrepreneur full-time reminds me of being in a secret club where the members only reveal the whole truth about how hard it can be sometimes to one another. It reminds me of the secret clubs of marriage and motherhood, where no one tells you how hard it’s really going to be until you’ve already joined the club. Thanks for lifting the veil for many people! I identify with lots of your points you outlined and it hasn’t been easy but it has been a great learning experience and definitely an adventure! I’d also like to add that though I can live/work anywhere, a lot of the traveling tiger blood I’ve had has been sucked into building my business–not in a bad way necessarily, but I find that I travel LESS now that I am working for myself full-time! Perhaps I was really just craving new experiences and adventure and I’m getting that–or perhaps I just don’t have the budget. :) Thanks for a great post!

    • Corbett

      It’s a great point Kaneisha. I find myself enjoying our “home base” much more now that I’m self employed. Partly that’s because I’ve been able to meet so many great people offline through connections I started online.

      Cheers and good luck with the business. It sounds like you’re enjoying the challenge, which is most of the battle.

  25. Thanks for writing this post Corbett. Sometimes it seems like successful entrepreneurs were born like that, like they didn’t struggle in the beginning.

    Thanks again for telling the other side of the story. I’m sure many people will be a little bit stronger after reading this post. Knowing that starting is not only hard for them. It’s tough for everybody.

  26. Corbett, this is the best article you have ever written. “Best” of course is highly subjective… but… best is how it feels to me right.

    Taking my main site through another convulsive redesign. Much gnashing of teeth. Again.

    And I found out why (at least some) people gain weight: it’s one moderately useful way to remediate “panic,” eat until comatose. =)

    • Corbett

      Wow Dave, thanks for that. This one felt great to write and publish. I love finding new ways to cover old topics.

      Good luck with the redesign. I always have fun with those, but yeah, they can be frustrating too.

  27. “If you’re seriously unhappy, don’t look to self-employment as a cure-all.” This quote really stood out to me. Talking with one of my good friends last month the happiness factor came up when discussing ideas for how to pursue my lifestyle design.

    When it came down to it, I hadn’t really looked at my happiness when it came to settling why I wanted to get out of my current job. I lumped in any aspect of my life that I couldn’t distinguish as truly making me happy as being part of what made me unhappy. In all honesty, that left a lot of stones unturned.

    I’ve since taken a step back. I’m trying to spend more time to turn over more of those “stones” and see if they are a contributor or a detractor to my happiness. The biggest stone has been my job. I plan on looking at it from as many angles as possible over the coming months. I’ll be working with my employer to see if I can make it contribute to my happiness instead of being a detractor. Otherwise, I’ll work on building my business then see how well it can sail.

  28. What a great article. So true indeed. A few years ago I started a cleaning company , after being on unemployment assistance for almost 18 months. It was great, at first, lots of contracts, great money….ahhhh..then I realized I had no proper accountant, no back up workers and I was working 90 hours a week, so much for living the dream!

    I closed one company and created another, dismal failures both. BUT, I learned from them made a list of all of the pros and cons and got excited, I believed I could succeed…it was there, I was just missing something.

    Once I figured out what I personally was missing, I reinvented me, not the wheel, but me, my thinking, my views, etc. I got down to business and started to see success.

    Was it hard? Absolutely
    Did my relationship almost break up? Indeed

    To get to Heaven, sometimes we gotta go through Hell folks.

    But we never succeed without failing a couple times, successful people have one thing in common, we never give up!

    Good luck to all of us!

  29. Hey Corbett. I’ve been reading you for a while and have never commented. I couldn’t resist on this one. So much of your work has been a big help and inspiration to me, but this particular post came at a time when I really need it. You just gave me the jolt I needed to keep powering through. Thanks so much, for this and all the others I never said thanks for.


    • Corbett

      Glad to be here at the right time Sara. Thanks for reading and good luck powering through!

  30. Excellent post. Here I was convinced I needed to get a backpack and some of those g*ddammed bare-foot shoes and board a plane to thailand before I could have a hope of being successful in my business.

    Turns out I should be myself, work hard, and build something people want to buy.

    Fabulous! I can sweat it out!

    Thanks Corbett. In a sea vibram’s and good intentions you shine through with heart and substance. And nicely dressed to boot!

    • Corbett

      God I hate those damned shoes. Glad you feel the same way Chase ;)

      • Corbett, we should find a way to make money off the internet. It would be fantastic, wouldn’t it!!?

        All we need is a computer and some internet. Not sure where they sell it, but I think my home depot guy was talking about some the other day so I’m gonna ask him.

        So excited to be planning for the “cyber” future together, holding each other’s hands as we first gently dip our toes, and then leap with abandon into the enormous bulk-heaps of cash that we’re going to make on internet!

        ¡Ansioso, ardiente, y con aspiraciones!

  31. Man I wished I had read something like this back then before quitting my job. Perhaps it wouldn’t have changed anything or perhaps going through the experience and discovering for yourself was the only way to go. In any case, nice write-up that really resonated with me on many points. Bookmarked!

  32. Kerry

    Excellent post, Corbett! I can’t believe how much you spoke directly to my experience (umm… maybe there are a few universals in there :) )

    1 – Starting a business while traveling – I moved from Arizona to Cape Town at the end of 2009 and since we could live comfortably in SA on one salary, I thought this would be the ideal time to start my business… and then I saw Cape Town. Why would anyone sit inside on a computer when they could be outside playing on the Cape peninsula?

    Yeah, spent a good 4-6 solid months being a tourist with my 4 year old in tow = no work accomplished (but lots of excuses for everyone asking about it back home.)

    Once I got over my initial tourist phase and settled in to living here things have gotten a bit more routine. Yet, I have definitely put my big African travel plans on hold while really ramping up my business.

    2 – Personal problems don’t just disappear – after my tourist phase I landed in my self-discovery phase (the stuff you can normally avoid when running the rat race as a working parent.) I would have told you at the beginning of this journey that I was not afraid. Whoa, did I learn that I had fears as one after another rose up and smacked me in the face. This was a fairly new experience for me and it pretty much killed any “working on my business” momentum.

    3 – Serious anxiety and panic disorders – I have only had the panic hit a couple of times, fortunately, but this journey has been concurrent with my adventure in to Crossfit and raw foods, so I think, shockingly enough, regular exercise and a good diet actually does help with stress :)

    4 – Your relationships may suffer – So in this process of discovering myself, I was completely unable to relate to my husband (who has a PhD in the sciences and who initially equated ‘entrepreneurship’ with “get-rich-quick-schemes”). Plus he seemed to not take my ambitions very seriously and got really funny about money once I was no longer bringing in a salary.

    It was like my marriage reverted to something out of the 1950’s the moment he became the sole breadwinner. There were many other dynamics and issues at hand too and it all boiled up and over and we separated.

    I am thankful everyday for that separation. It allowed me the space to get really clear on who I was, what I wanted and what I was truly trying to achieve, without someone else muddying the mix on a daily basis.

    We were apart for over 6 months (in a foreign country, while co-parenting our 5 year old) and I am happy to say through a lot of work we have managed to reconcile and create a much better relationship then what we previously had. No unicorns and rainbows, just yet, but a functioning, communicating family of 3.

    Additionally, since I gained so much clarity and made so much progress on my business creation while we were apart, he takes my work much more seriously now and those 15 different languages he can code in has come in super handy when I am trying to hack the CSS on my websites :)

    I will note that my now 6.5 year old son, is NOT thrilled to see mommy always on the laptop and we’ve had to work hard to make sure he doesn’t feel that he is second to my online activities.

    5 – Real chance the first business does not succeed. – My first two businesses never got off the ground. I had NO idea how to work for myself after 20+ years of working for others. I had very little contact with entrepreneurs when I started and the only ones I saw were online.

    My first two businesses, while on the right track, were not the right fit for my skills, experience and motivation. It took me almost 2 years to learn those lessons. But I learned and learned and learned.

    I founded a mastermind group with 3 acquaintances, all of whom were creating businesses for themselves and had experience working for themselves, who have now become friends, collaborators and my biggest cheerleaders (took action on this after reading your manifesto, Corbett!)

    I finally found the right setup for me and the right partners I needed to make it work. The ink is just now drying on those agreements and the 2 of them launch online in February, yet we’re already making money.

    So I left my last paycheck September 2009. I cannot believe everything I have been through since. And I wouldn’t change a thing. My plans for 2012 have already started to come to fruition and I feel as though it has been effortless (even though I AM working all the time.)

    I do very much acknowledge that my basic needs and those of my son’s were covered by my husband’s salary, so I never had that panic of how to pay the rent, yet his contribution was part of the risk analysis when I first went down this road.

    Hope you don’t mind the book-length comment. Your post struck a huge cord!

    Your posts here and Think Traffic have been instrumental in getting me out of analysis paralysis and taking action. Thank you!

    • Corbett

      Wow Kerry, you’ve been through a LOT over the past couple of years! I’m so pleased to hear that you’re still pressing on, and it sounds like your outlook has remained positive through it all. Most people would have given up I think.

      Thanks for the in-depth comment. It’s always helpful for me (and other readers) to hear about other people’s experiences. I’m so glad we have this outlet to share war stories and successes.

      Please keep us updated on your 2012 progress. Cheers!

  33. Love this post and totally relate. I have feared for the majority of the past year that I suffer from bi-polar- the emotions are so up and down with blogging. As it is my passion I have so much more invested in it which makes it that much harder.

    Having success in any field is by no means easy. It involves a lot of blood sweat and tears,. Many people turn to blogging thinking it is a quick money making solution, but unless you are totally passionate and committed to it, then I really suggest looking at other ways to earn a living.

    Jobs are not bad at all, and often I find myself craving a return to it, so that I know I have the security of money coming in and nights and weekends free. But then I remember who soulless I found the work and how much I love what I do now, so I keep on perservering.

    I think that is key to anything. All out massive action and perserverance. Its paid off for us.

  34. I’m attempting a half and half situation – I got sick of funding issues and contract renewals in my professional life so I took a fairly menial job, with hours just under full time. I’m now using that little bit of extra free time to start work on my own business. I honestly have no idea if I will succeed or fail, but in some ways I don’t mind either way – even if I fail, I’ll learn from it, so that won’t even be a failure. Either way, I’ve never seen myself working for someone else forever, so now is the time to try.

  35. Definitely can relate to this. Because of all those “lifestyle design” blogs, I had this magic idea in my head that if I moved to the Philippines where I could “travel to other parts of SE Asia!”, that building a business would be a nice transition. It’s been far from it. Yep, traveling and building a business does not work. Because I am on the negative most months and slowly trying to build an income (last month was my best month and this month looks even better so hopefully I’m doing something right and this isn’t just an anomaly). This process is humbling but I’m in it for the long haul!! I gave myself every chance to succeed (and fail!), by giving myself no other options. I HAVE to!!

  36. I wanted to point out the issue of social anxiety for new entrepreneurs. When you start your own business you set out certain goals and plans. If you meet those plans you are one of the very few blessed with a distinctive gab of vision.

    If your plans haven’t worked so far it is because you are inexperienced and your time was otherwise consumed in things that looked trivial at first.

    It is critical at this juncture to ask for help.I have seen a couple of businesses close around us just because they would refuse to seek help.

    Anxiety can be dealt with if the root is known. Starting a business is tough. However the resulting stress from not meeting goals or plans is not a problem without solution.

  37. “Liberty means responsibility. That is why most men dread it.” George Bernard Shaw

    I’m starting my own business, and even thought it’s not finished yet sometimes a lot of bad thoughts comes to my mind, I live in a very poor country and because of that many people have already settled for the little things they got, and when somebody starts dreaming high most of them will try to sink their dreams, it has been very though to me to stand still with my dreams, but sometimes the self sabotage habits comes to me and tries to make me stop, sometimes it takes over me but I am strong enough to shake it up and to continue walking.

    I all this is coming now that I am just starting and that I still have my job I can’t think of what will come to me once I make some cash out of it and get out of my job, but I never expected it to be easy, so I will keep on going.

  38. Tams

    Great article. I get tired of people on the outside tell me how lucky I am I have my own business. They don’t see me what at midnight I am doing accounting and putting marketing programs together. Your not an entrepreneur unless you are willing to fall flat on your face, pick yourself up and start again. After 10 years I now run 3 businesses, 2 with partners but it has been 10 years of hard work and lots of stress. For me I could never go back.

  39. I’m on the cusp of jumping from employment to self-employment. I’ve set everything up so I will still have a small income flowing in so my savings will remain untouched. This should relieve some pressure. I’ve also allowed myself two years to give this a go. I’ll be diving in head first and really going for the kill. I figure I’m not getting any younger and need to give this a try at least once in my lifetime. Either way, I’ve noticed one thing about pursuing a dream. If you can make it through the beginning stages, and never give up no matter how many times you “fail”, you’ll eventually make something happen. Like you said Corbett, you have to fight for it!

  40. #4 definitely hits home for me, as I’ve put business first, which is never good idea.

    #5 I think all business are a success, if you redefine how you define success.

    While a new venture may not yield the profit you are seeking, you’ve taken a positive step in the right direction, learned what NOT to do, and are one step closer to success.

    For me while my first venture didn’t pay out what I originally thought, it’s armed me with so many other skills that helped me land a job that pays 200% than I’ve made in the past.

    In that respect my original venture is a success and now affords me the resources to tweak original mistakes, become closer to debt free and branch out more.

  41. I think a lot of this lifestyle design digital nomad stuff that’s being pushed is dangerous.

    It suggests you can start a business without a base and just relying on tourist visas and doing visa runs the whole time. It also strictly speaking as the laws currently stand puts you in an illegal situation, even though there are arguments that can be put forward to claim otherwise.

    Would you be happy with that? I wouldn’t. I need a secure base to start and nurture a business. I can’t do that sitting in a hotel with noisy neighbours, weak and intermittent wi-fi etc, nor by sitting in coffee shops either.

    Basically you can travel – or you can start a business. Not the two together. Those who claim to have done it have often had some other form of support – a sponsor, have had a business already up and running to at least some extent and so on.

    Once you have your business systems built and sufficient clients then, yes, you can combine an online business with travel. Its probably one of the easiest business models of all for doing this.

    But for most people, trying to start a business and travel at the same time is one step too far.

  42. Hi Corbett, can you share with us how much savings you had before you quit your job, and how much savings you spent during your two failed attempts?

    Would love to understand more numbers to help us make a more informed decision.

    If sharing numbers is too personal, then how many months living expenses saved is also fine.



    • Corbett

      Hey Sam! Good to hear from you.

      I’ll put it in terms of what my savings could afford me. Your spending levels may be higher or lower than mine. When I first jumped into entrepreneurship in 2006, I worked for a few months while also working on a startup idea. Then I decided to quit my job and work on the startup full-time. At that point, I had enough savings to fund that lifestyle for probably around 3 years.

      BUT, there’s a big difference between having the savings and being mentally prepared to spend it. I was definitely not comfortable with spending all of my savings. During that first year, I lived off savings for about 10 months. Then we found investors and I started earning a modest salary.

      Fast forward to 2009 and I decided to take a 6-month sabbatical. It ended up lasting 8 months. On that trip I decided it was worth living off savings again until I built something solid for myself. I spent probably another 15 months of savings before I had much significant income during 2009 and 2010.

      All told, our savings supported us (I’m married and my wife is an artist) for about two years. My wife worked and sold paintings during the parts of that where we weren’t traveling. It supplemented what we lived on but it wasn’t enough to live on entirely. As an artist, she’s essentially in long-term startup mode as well.

      Along the way we ended up learning how to be frugal and how to make our money last longer. We ended up spending over half of our savings, and I think the investment was completely worth it. Definitely nerve-wracking during the process, but our lifestyle now is worth so much more than that.

      Does that help Sam?

      Every situation is different. It really depends on your resourcefulness and your willingness to spend what you’ve worked for in pursuit of something else.

      • Very helpful Corbett! That must have been nerve-wracking to spend your savings during start-up mode, but it definitely sounds worth it. What’s the point of saving anyway? For moments like these.

        3 years of savings is a good target, and I originally had 3 years as well in my “Quit Your Job, Die Alone” post on But, I brought it down to 2 years, as I was thinking it’s do or die for your start-up by end of year 2. It was the rubber point where going on after 24 months with no results might be disasterous long-term.

        I totally hear you on being able to spend savings. I don’t think I could do it….. and only the interest income, which even then, seems kind of painful!

        I’m seriously contemplating making a move this year to work FT online since it is so much FUN! There’s a lot of untapped potential for the Yakezie Network that needs someone 100% dedicated to it to achieve. We shall see. I’m excited!

        Best, Sam

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