Corbett Barr

Lifestyle Business Weekly

How To Get Past “Where Do I Start?”

It took me a little longer than I hoped to start earning a living online, but things are finally happening. If you’re stuck at the beginning and not sure how to start, this post is for you.

At some point last year after some soul-searching on our sabbatical, I decided what I really want career-wise is a lifestyle business. I don’t want employees or a permanent office. I don’t want regular meetings or investors, and I want to be able to work from anywhere.

The problem I faced is that knowing what type of business you want doesn’t make it magically appear overnight. Deciding is only a tiny first step. A very important step for sure, but really just the tip of the iceberg.

In fact, calling identifying a goal or making a decision a “step” might actually be starting out on the wrong foot, so to speak. If your goal is (like mine) to build a business that supports your lifestyle, all the goals and decisions in the world won’t cause any real progress.

What you really need is action.

It’s hard to start executing right away though. And so, most of us spend months and months reading books and advice, checking out different business models and trying to find out how others have done it.

Some level of study is important. If you just jump into building a business right away, you probably won’t get as far as you would if you had learned a little first. On the other hand, it’s easy to get stuck in the analysis phase for months or years.

Where is the balance?

Don’t worry, I’m not talking about work-life balance here. What I mean is, what is the right balance between learning and doing in entrepreneurship?

How much learning should you do before you start doing? Can you do and learn at the same time?

I’ve read a lot of great quotes recently on Twitter and on blogs about this very topic. One of my favorites was from Sonia Simone in a recent Copyblogger post:

Inspiration is great, but execution pays the bills

Another of my favorites is from Lao-tzu (c 604-c 531 bc), founder of Taoism:

The longest journey begins with a single step

How much time you need to spend purely analyzing business models and success factors depends partly on your experience. However, don’t get caught in the trap of thinking your first business needs to be perfect or that you only get one chance.

At some point, you can (and should) learn as you go along. Take that first step, and then study how you should take your next step.

Think of the balance between learning and doing like taking an extended trip. Before you embark on your trip, you will probably research the places you’re going, book your flights and probably book your accommodations. Maybe you’ll even buy tickets to some events ahead of time.

What you probably won’t do is plan every day’s events ahead of time (if you’re that type of person, you might have a hard time as an entrepreneur). For most people, it just wouldn’t make sense. You need to get to know a place before you can best plan what to do each day. If you planned everything ahead of time, either you wouldn’t have the best time on the trip, or you’d spend a lot of time re-planning.

And when your trip is over, you’ll take what you learned about traveling to that destination (and travel in general) and use the knowledge to make you next trip even better.

And so it is with starting a business.

You can’t possibly plan every aspect of the business ahead of time. At some point, you just need to get started because there are certain things you can only learn by doing. Maybe this particular business won’t succeed like you want, but what you learn from it will get you closer to your goals the next time.

The only way to completely avoid failure is never to try. Luckily, failure is often the best teacher.

Things will start to work out, if you try.

Here are two of my favorite fundamental rules of success:

1) Try.
2) Repeat #1 until you succeed.

The hard part is getting through that period where it seems like you’re not progressing at all. The bigger goals you set for yourself, the harder it will be to keep trying.

Knowing that failure is an inevitable part of success and that you have to learn certain things by doing, one smart course of action is to first start something with modest goals.

If that thing you start flourishes, congratulations. Take what you started and expand on it.

If the thing you started doesn’t succeed, don’t worry. That’s why you didn’t sink your entire life and fortune into it. Close up shop and start again. What you learned from the failure will help you next time.

That’s the philosophy behind “Affiliate Marketing for Beginners, Complete Beginners and Future Tycoons,” the product I’m putting together right now. I want to show you exactly how to make your first dollar online through affiliate marketing.

I’m not going to try to show you how to make “six figures in six months” or anything like that, because a) that isn’t what you need, b) that isn’t completely realistic in the beginning and c) I’m not the right guy to teach you that (yet).

Instead, by helping you with a modest but realistic goal of making your first dollar online, you will achieve much more. You will have taken action, started a real business, learned along the way and prepared yourself for your next bigger venture.

I’m not saying that you’ll all become big-time affiliate marketers. Although some of you might (it is a $13 billion industry). Either way, learning how a complete business works online in a relatively short period of time (about 60 days) will help you see how a much bigger business could be built too. A business that could actually support your lifestyle goals. It’s kind of a Mr. Miyagi thing, you know?

That type of small but persistent action is what has made things start to click for me. Instead of trying to create one big perfect business with a lot of pre-planning, I’ve been taking a lot of little steps and learning as I go along.

And now, 8 months after I returned from a life-changing sabbatical, things are starting to work. I’m earning money through affiliate marketing, from consulting and I’m working on a fantastic first product. I started a new business that people are excited about and that I’m really having fun with. I can see my ideal lifestyle design coming together now, if I just keep trying.

Things are happening, momentum is building and it’s all due to a lot of small actions I’ve taken over the past year. For me, the right balance involves more doing than learning, and it probably does for you.

I hope to help you get past the “where do I start” phase too.

What do you think the right balance between learning and doing is? Please share in the comments!

photo by Un ragazzo chiamato Bi

Corbett Barr

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


Why Lifestyle Design Alone Isn’t The Key to Happiness


Ask The Readers: What’s the Best Way For a Beginner to Get Started in Online Business?


  1. Corbett,

    This all must be quite exciting for you. Things are going to be a little scary for me for abit, but I’m sure I’ll figure things out. After months of just think and planning, I finally started my blog. I’ve been learning a LOT of stuff and am embarking on affiliate sites/marketing, which I turns out successful.

    Many people just sit and think and try to learn everything in hopes of getting it all down so they don’t make any mistakes. I was that way. People need to just “do” and only then will they learn and succeed.

    • Congrats on starting the blog and getting moving, Moon. If you’re human, you’ll make mistakes, but it’s nothing to be afraid of. Good luck.

  2. “Action is a great restorer and builder of confidence. Inaction is not only the result, but the cause, of fear. Perhaps the action you take will be successful; perhaps different action or adjustments will have to follow. But any action is better than no action at all.” – Norman Vincent Peale

    I hear you Corbett. I really do. I’ve been stuck in the “analysis” phase just like you described for months now (thank god not for years!). Where should my focus be? How many blog posts do I need in the beginning? Is my social media strategy top-notch? Does anyone even care about these things I’m interested in? Can I make a living with this someday? If yes, then how.. you get the picture.

    I decided I’ll participate in the 12 week challenge (, put together by Lea and Jonathan Woodward from and finally launch the blog I’ve been hustling around for months now ( What’s been taking so long are all the other nomad couch and “nomadic entrepreneurship” related side-projects I’ve been working and tuning around the clock (sometimes literally). “I want this to be perfect..” “I don’t have that and that yet and I’m still researching around this subject”. “What about the business side of this? Is my business model ready and the RIGHT ONE, when I get to that phase”. Damn what a vicious over design cycle this can become if one let that happen (and I did)!

    Not anymore, it’s action time! (I’ll be launching Nomad Couch on next week’s sunday 11.4 at 6pm EET). Sorry for this outrageous “hidden” promo. Feel free to delete it from the comment. Just felt like it’s time to officially give a date for launch so I can’t give myself any more excuses to back down now! :)

    Thanks again for this great post! What a great inspiration once again!

    • Great quote, Juha. Congrats on the upcoming launch. Please send me a reminder on Twitter or email when it happens.

      • Thanks, I’m very excited about next week! My god.. I just checked how many posts drafts I’ve done from the very first day I started preparing NC for a launch.. 56! Yes, fifty-six. That’s insane. Been so worked up and amped about the blog that I’ve written down dozens of post ideas, but still haven’t yet lauched the damned thing! Well, at least I should’t have too many problems in coming up with a new post ideas now :)

  3. Corbett,
    I battled with action for a long time as well. I have so many ideas, but have a hard time chipping away at those first few vital steps. The biggest thing I’ve learned is to throw my perfectionism to the side and just start. Get something up even if it’s crap and tinker it as you go.

    I am so excited to see the latest developments on your other site. It’s good to hear that your hard work is paying off! I feel like I am finally getting to the point where all the doing I’ve been doing is starting to pay as well.

    Building business is not an easy game and the more support the better. Thanks for sharing your experience and inspiration.

    • Perfectionism can be a real hindrance, right? I always feel much better when I push those tendencies aside and just do something, flaws and all.

  4. Hey Corbett!

    When I opened this up this morning to read it, I was thinking, “Did he just read my mind?” I just decided this week that enough is enough with the research!!

    While I’ve had my blog(s) up for a few months now, I’ve been doing a lot of research, and obviously there is way more information on the internet than any person could research in an entire lifetime. I’m pretty good with deciphering what is important, I’ve started one fantastically successful business before, but online business are a totally different animal. I’ve felt a little trapped in this vortex of information.

    But like I’ve preached to others, you don’t know unless you try, and failure is going to be your best indicator for the direction toward your right path! Obviously if you keep going down the wrong path, you’ll find the right one. Also, as a seasoned business owner, I realize the value of “buying expertise”, which is another way of “buying time”. So if I don’t have time do dig deep in the trenches and study, I can hire someone who has already done that, and utilize their knowledge. I don’t have to know it all….nor will I ever!

    I love the attitude of “how can I?” Brilliant post and excellent content as always!
    Have a margarita for me!!


    • Welcome to the other side of the “vortex of information,” Makenzie. I like your attitude of buying expertise, and knowing that you don’t have time to do (or learn) everything necessary. Please let us know how things progress here.

  5. Joe

    Corbett, thanks for spelling it out!

    A couple of weeks ago I started my blog. It felt good to be just getting on with it. I figure that I’ll learn much quicker if I’m actually taking measurable steps forward at the same time. Originally I didn’t want to start my blog until I knew exactly what it was going to be. Now, I’ve embraced the idea of fine-tuning it along the way.

    I know it’s going to be a long and tough journey, but I’m enjoying it all the more now that I’ve passed the starting post.

    • Yes! I started this blog last year on a bit of a whim. It has grown fantastically since then, and I’ve learned more than I could have imagined. Free Pursuits is much different than it was when I started, and I continue to tweak things as necessary. Good luck with the new blog, Joe.

  6. Great Post Corbett, especially your fundamental rules for success. It really does come down to that little formula. Brilliant!
    Looking forward to hearing more about what you are working on ;-)

  7. I tend to read to a point when I can’t stand just reading anymore. When I was a personal trainer, I did this with my clients, too, get them walking until they couldn’t stand just walking anymore and HAD to run. That first step is so hard, but knowing that inspiration is there to start the fire, and you have to start running to keep it going. And the beauty of it is, you can always go back to the learning stage when you get stuck, the books don’t go anywhere, you can always take a walking break to check back in. Just finding your momentum and grabbing it when it shows up, whether your head thinks you’re ready or not.

    I’m excited to see how this affiliate marketing program turns out! I haven’t done any research into affiliate marketing…perhaps this can be a good inspiration!

    • That’s a good way to do it as well, Andi. That is, assuming you ever get to that point where you’re sick of reading. I think some people could read forever without feeling the urge to take action. But yes, you can always go back to the learning stage at any time.

  8. i like it! Although i would revise your steps to success to take account of the philosopher Yoda’s wise words – do not try, do. Like you said it is all about taking action.
    Step 1: Do
    Step 2: Repeat step one

    Trying is the quickest way to failure, doing is the path to success – it is all about your mindset. I’m not trying to develop a successfu blog, i am developing a successsful log!

  9. Thanks for the post… I was thinking along the same lines when I finally started posting on my blog again after 1.5 years… it doesn’t need to be perfect, but it does need to be started! I enjoy your writing!

  10. Ed

    some good things you can do is try many monetization options and see which works for you

  11. Hey Corbett,

    I definitely spend more than my fair share learning rather than doing. I think it’s a tough thing to balance, and I shoot for spending a small amount of time “ramping up” my learning (e.g., perhaps 1-2 weeks of focused reading and research) and once that’s done – I just go forward, and allow myself 20-30 percent of my time to continue research, while the other 70-80% needs to be spent doing

    Once I get some level of proficiency “doing” (even if it’s not *that* proficient) I tend to enjoy that more anyway, and the ratio swings to where many weeks I’ll spend 90-100% of my time doing, since I have less questions (though I may just be blissfully ignorant heh) and am enjoying actually creating =)

    • Thanks for sharing your ratio and approach, Sid. I probably spend about 70% doing and 30% learning still. I enjoy learning, so it’s hard not to do it, even if more action is necessary.

  12. Hey Corbett!

    How are you doing Sir? It’s been a while!
    I totally agree with you. I also thought it would be relatively easy to make money online, but only now, after 2 years am I starting to make decent progress towards my goals online. I think it will take me another 2 years before I get to the point where I want to be!

    There are of course people who make a lot of money online within the first few months, but usually these people are:
    Far and few between
    Very smart
    Or have prior business/marketing experience

    Of course, that is not to say that it can’t be done, but rather expect to spend a lot of time and effort before making a good income from online. If it happens sooner, it’s a pleasant surprise :)


    • Hey Diggy, thanks for stopping by. I would have thought you started working online more recently (you just seem like one of those guys who “gets it” quickly). Even still, two years isn’t really that long. Think about how long it takes someone to enter a new traditional career. College + specialized training + apprenticeship. Taking 4 years to earn a living online doesn’t seem very unreasonable to me.

  13. Nice post Corbett. You’re right – a lot of people can get stuck. Paralysis by analysis as they say. On the other hand, research shows that the more time spent in planning and contemplation, the more lasting the change will be that you make ( Sorry for the plug but the article really does relate. I guess as Sid said, the trick is in the balance of thought and action.

    • Interesting research, Carmen. I hadn’t heard that before. It makes sense, but what about the people who never leave the planning/contemplation phase? And what about the success of future endeavors for people who acted earlier?

  14. What a great post! I think that there is a delicate balance between learning and doing. I’ve been doing a mixture of both for the past 5 years or so. I’ve failed at a lot of things, and I’ve done ok at others. Right now I’m working on a project that I believe has the best chance of fully financing my lifestyle within the next 10-12 months. And that wouldn’t be even close to possible had I not failed soooooo many times. I really think that you have to sort of pay your dues online, unless you have a really great mentor or something. You definitely know that though, since you’ve taken part in so many different projects and businesses. Once again, a great and refreshing read.

    • Awesome, Nate. Congrats on your new project. I hope you can share some details with us as they develop.

  15. Profound words, this is a great blog. This post has just cemented my drive to the top. Thank you.

  16. Annie Stith (Gr8fulAS on Twitter)

    Thanks for the inspiration! I’ve been reading and watching for about two months now. I think it’s time to start with a good, small idea that will lead to my bigger, not quite ready idea, and start building up experience so they’ll both be successful.

  17. I both did a graduate degree in Leadership/Entrepreneurship, and wrote a book about it. I do come at this from an academic perspective, but in reviewing over 300 pieces of research and literature on entrepreneurship it was found there was no solid definition of what an entrepreneur was. No one could agree. So I created one that applies, here:
    “An entrepreneur is a person who identifies an opportunity in the market and acts on it.”**

    Identifying an opportunity in the market makes you perceptive. Acting on it makes you an entrepreneur.

    I’m a victim of this, myself. Hell, I did a business/marketing degree and a graduate degree, and researched and wrote a whole book… research & analysis, ad nauseum. And I still don’t have an active business because I haven’t taken action on anything (except acting on doing more research/writing). I’m working on changing this. (Mind you, I’ve started 3 companies in the past that ultimately failed… and that fear has led to a desire to over-analyze on the hope I won’t repeat the failure).

    One other thing I’d like to mention is the idea of planning. I don’t know that I agree with the assertion that more research and contemplation will make changes more lasting. Contemplating and research is, of course, helpful. But there is a point of diminishing return. It’s not hard to get something 95% right, but that final 5% of “perfection” is exponentially more difficult. You’re better off starting when you have 95% of the information and correcting course along the way. It’s the “Ready, Fire, Aim” concept. And to throw the academic stuff in there, research on the effectiveness of business plans is very inconclusive. What I found is that, basically, any plan will increase your likelihood of success, but a plan jotted out on a napkin or a 3×5 card has as much likelihood of success as a 50-page business plan. The latter may be necessary for venture capital/bank funding, but the plan on your 3×5 card has just a high likelihood of succeeding.

    (**Note: this is a practical variation of the exact definition I used in my academic work).

    • Awesome contribution to this discussion, Brandon. Thanks so much for sharing the well-researched and academic point-of-view (as opposed to my speculative and experiential one). I love the fact that a plan is important but the size of the plan doesn’t matter.

      I too have started and buried a few businesses in the past, and I completely understand how the fear of failure can influence your actions. One way to mitigate that is to identify and minimize the consequences of failure before you get started, so you know exactly what you should be afraid of.

  18. Hey Corbett,

    I’m a first time reader and I must say, I really enjoy your stuff. You officially have another subscriber! It’s refreshing to read something with such candor. If it were easy to run an online business and get rich, then everyone would do it. There’s no easy way!


  19. Awesome, Greg. Welcome! Candor is my game. There’s enough hype out there already.

  20. Right on, Corbett . . . we do often fail to just take that ACTION step! Thanks for the great stuff you’re putting out!

  21. Great post Corbett. I had this sitting in my reader for a few days without reading, but I’m certainly glad I did. The paragraph about building a lifestyle business was particularly resonant for me as that is my current main goal.

    Keep up the great content across your sites. Thanks!

  22. What if you want to run an online business from anywhere in the world but you dont have a business idea and you dont want to get into solid Affiliate Marketing? What do I do then?

    • That can be a great option. I earn the majority of my income through affiliate marketing currently as well. I’m actually putting together a complete “affiliate marketing for beginners” course right now that I hope to have ready within a few weeks. If you’re interested, you can sign up to be notified when it is ready here:

    • Oh, just noticed I read that wrong. Man, I have to slow down a little. Anyway. If you don’t have a business idea AND don’t want to do affiliate marketing, hmmm.

      In the end, an online business is going to be about selling products or services (or selling someone else’s products or services), or producing content that advertisers will want to sponsor.

      I think you’re going to need to do some soul searching. Running a business online will take guts, determination and patience. I can take over a year to get anything meaningful going, so you need to choose something you enjoy. What are your passions and interests?

      Another option might be to find location independent employment for now. It does exist. Employers are starting to care less about where you work, as long as you get the work done.

  23. This is exactly the post I needed to read. I have been planning for almost 10 years :-(
    Time to get to work! :-)
    One of the most important things I have realized is that I don’t NEED location independence I just want a lot of time flexibility.

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