Corbett Barr

Lifestyle Business Weekly

The Hardest Thing About Lifestyle Design


Quick, what’s the hardest thing about lifestyle design?

Is it finding an income source that’s compatible with your goals? Is it the logistics of making your life work while traveling? Is it finding the courage to leave your job? Is it getting your spouse to agree with your crazy dreams?

Those things are all hard, but they aren’t the hardest thing about designing your own life. I’m sure you can think of a dozen other things that all seem like the hardest part of reaching your goals.

The way I see it (having been self-employed for over three years now) is that the hardest thing isn’t a tactic or a strategy or attaining some knowledge or even being lucky or creative enough.

The hardest part of lifestyle design is winning the mental battle that threatens to make you quit every day.

It’s all about beating self-doubt.

Do you know what I’m talking about? If you’ve already committed to living an unconventional life and pursuing your dreams, I can’t imagine that you don’t also experience what I’m referring to. I’m talking about that conversation you have with yourself every day about whether you’re doing the right thing. At its weakest, that inner conversation is just a nuisance that makes you a little less productive for the day. At its worst, that conversation leads you to thinking you should just throw in the towel.

What it comes down to is simply self-doubt. That doubt takes many forms. Maybe you think you’re not smart enough, or savvy enough or you don’t have the right experience. Or maybe you think you’ve made the wrong decision and that you’re wasting time chasing uncommon goals. Maybe you start to want what the status quo offers, because it’s the easy way out. Maybe you think you don’t have anything original to say, so why bother?

Here’s a secret about that battle with self-doubt you’re having: everyone has it. Well, maybe not George Clooney, but everybody else. Seriously, I have thoughts of self-doubt every day. Some days I have to talk myself off the ledge. It all depends on how I’m feeling and how out-of-control I let the inner dialog get.

I’ve definitely let it get the best of me at times over the past six months since starting this blog. I’ve procrastinated, wasted time and not focused on what’s really important. I think that happens to everyone (again, maybe not Clooney), and the successful people are the ones who can limit the damaging effects of self-doubt.

Lately, I’ve been getting better about knowing that the self-doubt is inevitable, and that what’s most important is how I handle it. Sometimes I can’t really control it, but I know that I just have to get through it and not make any rash decisions while that particular voice has strength.

So, what’s the antidote to self-doubt? How do you keep it from stealing your dreams? The three critical components to beating self-doubt are: awareness, passion and perseverance.

Understanding the Problem and Staying Vigilant (Awareness)

Admitting you have a problem is the first step in any good recovery program, right? This is no different. And, luckily for you it affects just about everybody. Try having a conversation with a friend about it. You might take comfort knowing that they go through many of the same self-defeating motions.

Once you are aware of the problem, you can change the way it affects you. Instead of seriously having the conversation with yourself and letting it take you to the edge, you can look upon the feelings as an outsider and know that you just need to let them pass. This is quite liberating.

Another great thing about being aware of self-doubt is that you can start to recognize and avoid the things that set you off. For example, I noticed that I had a slight addiction to checking website statistics, both for myself and for other websites and blogs I’m interested in as a comparison. I found that I was checking those stats often because I got a small rush whenever my blog had an increase in visitors or subscribers or whatever. The opposite happened whenever the stats decreased.

This daily yo-yo of feelings isn’t good for my psyche. And, it doesn’t even make sense to check things so often because daily fluctuations are meaningless. So, I did myself a favor (not to mention reclaimed some wasted time) by resolving to check stats only on a weekly or monthly basis. I still haven’t completely conquered my addiction, but I’m working on it.

Having the Courage of Your Convictions (Passion)

The next critical component to winning your mental battle is having the courage of your convictions. What does that mean exactly? It means having the confidence to do or say what you think is right even when other people disagree.

At some point after you’ve formulated your current world view and personal goals, you need to “lock them down” and start standing up for what you believe in. If you don’t, you’ll find yourself spiraling into a canyon of self-doubt every time someone disagrees with you or presents a compelling argument in favor of something else.

In many ways, having the courage of your convictions is related to passion. Being passionate about reaching your goals will help you stand up for what you believe in and stop letting other voices call your dreams and goals into question.

Not Getting Bored (Perseverance)

The final component to beating self-doubt is perseverance. For me, this is a matter of not getting bored. I have a terrible problem with getting bored easily and moving on to the next project because I enjoy the rush of starting something new.

If you let yourself get bored with the goals you set or the projects you’re working on to make the goals possible, you’ll be far more susceptible to self-doubt. At some point, you’ll be too weak to defend your dreams from the doubt, because moving on is what really interests you anyway.

I can’t say I’m an expert in overcoming the “not getting bored” factor yet. I do know that I’ve abandoned plenty of opportunities and projects that in hind sight would have been successful if I had just stuck with it. Perseverance is a big part of success, and you need to be confident that your goals are worth spending time on, even when they aren’t sexy and new any longer.

If you have tips about perseverance, or any other aspects of defeating self-doubt, please share them with everybody in the comments!

Thanks to Man Vs. Debt for inspiring me to look into what’s really holding me back as a blogger and lifestyle designer. His post on how not to suck at blogging is a great kick in the ass. Read it and you will improve.

photo by addicted Eyes

Corbett Barr

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


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  1. Jen

    Great post Corbett.
    Lifestyle design is unchartered territory and it’s great to have the community that’s out there and advice from other bloggers such as yourself. Thanks for sharing what’s been holding you back so honestly – I can identify with alot of these (particulary confidence and persistance). This area is a great personal development experience in itself isn’t it? I notice my belief in myself and persistance has definately increased :-)

    • Thanks, Jen. It really feels good to share openly. And I think that self-doubt and everything we’re talking about really applies to anyone who strives to live an out-of-the-ordinary life. It really first started hitting me when I became an entrepreneur (long before I knew about lifestyle design as a topic).

  2. I owe a lot to other lifestyle designers. I have learnt so much from them as they’ve gone before me. They share their experiences through their blogs and remind me that I’m not alone in lifestyle design.

    • I feel the same way, Gordie. There are so many great people sharing their experiences that I feel supported at every step. I just have to remember to reach out when in need. Thanks for contributing to the community here.

  3. Great post! I totally agree with you. The biggest change you have to make is in your mind. At the end of the day your life is a reflection of what you believe you deserve and what you think fits your self-image.

    Change your self-image and what you believe you deserve and you’ll start working to make your real life situation reflect that.

    • Yes! “What you believe you deserve” is a huge can of worms, isn’t it? We all have perceived limitations at different levels in different areas. If you can’t see yourself really doing something, you’ll defeat yourself anytime you get close.

  4. Wow Corbett, I couldn’t identify more with this post. I feel the same way too. I think all bloggers have a point where they feel like they want to throw in the towel at some point, but like you said, it’s all a test on your self-doubts, and if you’re a person who is willing to persevere through those the toughest times and get out it.

    • I’m sorry you identify so much with the post, Tristan, because I know how tough that makes things for you ;) Different people wrestle with different amounts of self-doubt, and at times I wrestle with a lot. Over time, it gets better, especially as I connect with people trying to reach similar goals. Thanks for writing.

  5. I’ve found that the more businesses I set up, the less I get that ‘talking myself off the ledge’ feeling. It may be because each and every time you make fewer mistakes, or it may be that you just start to get numb to the bad feelings that come with making mistakes (especially since the lessons learned mistakes are the most valuable asset an entrepreneur can have!), but slowly and surely those bad feelings are wafting away and a more Clooney-esque vibe surrounds me every time I think of doing something new/foolhardy/adventurous. I think keeping those 3 concepts in mind will help expedite that process, though!

  6. I can relate very strongly to your feelings of self-doubt. I struggle with this everyday, and it makes it even harder that I haven’t “made it” yet. Should I just give up? No way. I really like how you mention awareness as part of the process. That is often overlooked, and I personally overlooked it myself at first. Lots of good info here, Corbett. And by the way, Clooney can’t be perfect, there’s no way!

  7. The power of self talk is immense. Keeping a negative word track in your head can have powerful consequences for sure. Good advice here to be aware of that.

    Combine positive speak and passion and you are well on your way!


    George (former lurker) :-)

  8. Great post Corbett! Really gets to the core of Lifestyle Design challenges! Like your Awareness, Passion, Perseverance tactics! Good luck! Bernie (blogging at Management Sushi)

  9. Corbett,
    Great thought-provoking post. I certainly join the list of self-doubters but I try to “persevere” through that self-doubt. I think you have to challenge yourself to get over the self-doubt by taking action. One action I recently took was to pursue the guest-posting avenue on other, more successful blogs. Surprisingly to me, my submissions were accepted. This has given me a renewed sense of exhilaration toward freelance writing, which is where I really want to be.

    Thanks for this post.


  10. Jim Ireland

    The best post yet. I worked with Corbett at Wafertech back in the 90’s. He was a quiet, reserved, very competent guy. I had no idea there was so much knowledge under that calm surface. This post shows a maturity well beyond his age.

    If I was 24 or 34 instead of 64 I would really be tempted to follow this path. Instead I’ll watch and see where it leads.

    I am looking forward to seeing the new site with your portfolio to get an idea as to how you make money.


    • Thanks, Jim. 10 years is a long time, especially from college kid to self-employed 30-something ;) Thanks for joining in the conversation.

  11. This post really strikes a chord in me. I feel that the mental battle of self-doubt not only applies to self-employment or business; it definitely applies to everyone in all walks of life. Of the three components, I think passion or more importantly COURAGE is the most difficult to achieve and the most essential. Overcoming fear and doubt doesn’t happen overnight. It takes many small steps towards forming better habits that develop confidence.

  12. I knew what the answer was before I got to it, but you said it a lot better than the voice in my head did :-D

    I think you’re being fooled if you think Clooney doesn’t have those kind of thoughts at least every now and again. They are probably the most prevalent and motivating factors in most peoples’ lives, no matter which direction they let those voices motivate them.

    Good to see you are letting it motivate you in a positive way. You have a lot of good stuff to share.

    • The direction I’m most afraid of the voices taking me is really no direction at all. That’s probably the most common outcome for people, where your thoughts bounce back and forth between ambition and doubt, leading you to do nothing.

  13. The link you just tweeted ( about Entrepreneurial Manic-Depression was exactly what I first thought about when I saw this post.

  14. Great article, Corbett! Be passionate, stand up for what’s important to you, and dance like nobody is watching. I fight similar battles to yours every day, but I wouldn’t want to be standing anywhere else either. Thank you!

  15. Hi Corbett,

    Here’s another perspective on self-doubt: very often, that inner voice isn’t even ours. Listen closely, and you may well realise that it actually belongs to a parent, a sibling, or your high school math teacher…

    Once you recognise that the self-defeating messages were sort of “pre-recorded” by your family or your upbringing, it becomes easier not to take them at face value. It certainly beats the stress of feeling like two sides of your own brain are waging battle against each other!

    Thanks for your thought-provoking post,

    • That’s a great point, Emmanuelle. I hadn’t really thought about the “pre-recorded” origin of self-doubt. I’ll keep an ear out for it from now on!

      • That really is a good way of saying it. We learned it from someone, other than experiences like sticking our fingers in a flame to learn that that means “HOTTT!!!!”

  16. I think it is important to remember that most people have doubts about the effectiveness of their actions. Nothing in life is certain so we don’t know if we are wasting our time our not.

    There is no blueprint for life. We are all making it up as we go. Sometimes we get lucky and succeed beyond our dreams. Sometimes we can’t get ahead no matter how are we try.

    I think self-doubt is healthy. It shows that you don’t know all the answers and are willing to do the work and try to improve. People who think they are already great are the ones who tend to stop growing as individuals.

  17. Great post. I’d add there’s another issue beyond just self-doubt – it’s facing up to the responsibility of how we actually use all the time we have, period. Once you throw away the routine of a regular job, it’s then up to you not only to fashion your own career, with all the responsibility that entails, but it’s up to you to figure out how to spend your time from day to day. You have total responsibility for your own actions.

    Focus and discipline are the two key things anyone who is self-employed needs to succeed – and these are both important in pursuing bigger, more significant life goals too. This is the awesome part of becoming self-employed – it’s also the scariest part, because focus and discipline are two really hard things to master continually, day in, day out. I think it’s what trips a lot of people up – it still gets me 7 years after starting out on my own! (Indeed, perhaps I should be working rather than leaving blog comments…)


  18. John makes a great point in regards to self-doubt keeping us in check and growing. I tend to think it’s somewhere between the two extremes (ha! aren’t most things?) and the point you touched on about awareness is key. I find that self doubt really creeps in when I’m following someone else’s path and trying to make it my own. We’re raised with all these ideas of what’s right and what works and the way we should walk, etc. When you choose to jump into an unconventional lifestyle or entrepreneurship you reject those ideas and are left flopping about a little haphazardly. The best thing you can do then? Choose the path of least resistance and follow those who have made the unconventional lifestyle work before.
    I’m in full support of following what other people have done and learning from their mistakes, but I never feel really confident in what I’m doing until I’ve shed the pre-conceived notions that their way of living unconventionally is “unconventionally right.”

  19. Passion is always where I seem to lose myself. I get distracted with so many ideas or discouraged that the ones I have are so lame I should stop trying. Not true…and keeping passion alive is the crux of following through for me. Thanks for reminding me of that Corbett

  20. Mar Higuera

    Plain thanks for the honesty! I missed that when I lived in the Valley… everyone just pretending to be so happy and have such perfect lives&jobs

    It is hard to go against the current, and I would agree with previous posts, a big part of it is just someone else voice, everybody else as a matter of fact!

    Acknowledging and sharing, I think, is the first part to let it go and just carry on following the pulse of your own heartbeat…go on and continue inspiring us!

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