57 Comments / last updated August 21, 2019

Take More Risks, They Said.

“Take more risks,” they said. “It’ll be fun,” they said.

I’ve been around business people all my life. And the one thing you notice is that the successful ones take risks.

But not everyone is built for risk taking.

Personally, I hate risks.

I just want to sit in my local cafe and write blog posts and not do anything that could be even remotely stressful.

So why do I end up taking risks anyway?

And has it had a big impact on my business?

You bet.

Why I wanted to take more risks

I’ll just put it out there.

If you get anxiety you usually don’t want to take risks in life.

But then the flip side of that is that by not taking risks you end up never changing your situation and the anxiety ends up getting worse.

It’s hilariously painful.

Today, however, I just want to talk about risks relating to my business.

The business of blogging.

If you read my article on things to know before you start a blog you might have noticed the bit at the end where I talked about 2014 being the year where I decided to be “prolific not perfect”.

That was my way of telling myself that I needed to try more things, put more articles and ideas out there and not spend so much time polishing the last 1% of my projects because, in truth, that is a total waste of time.

And I was doing it because of nerves.

Sure, my blogs were successful at the start of 2014 but I really wanted to amp it up. I was watching mates like Glen testing out new things and absolutely killing it. They were taking risks while I was kind of plodding along safely.

Well, I wanted a change.

Why taking risks really, really sucks

At the start it is really hard to take risks.

It is a challenge.

And sometimes that challenge sucks.

Yes, things go wrong. Your launch might be a huge failure or the marketing campaign that you’re working on might get no returns. You might lose subscribers or even precious Google rankings.

And that hurts.

But it seems to me that the really sucky part about risk taking is the build up in your mind.

The actual event is never as bad as the worry you attach to it beforehand. (Tweet this quote)

In fact, if you can get past that mental stuff you often find that the “risky” part is often not that bad.

Even better, you start to see it as the fun part.

Why we want to take more calculated, informed and clever risks

I’m not here to tell you to take stupid risks.

If you have a family to support, debts to pay off, etc. then you want to make sure that you are being clever about any risks that you take.

That means getting advice from professionals, weighing up the situation for yourself, and not going in fast with the hope big pay offs.

This is business, not gambling.

On this blog I always try to speak from personal experience. And for me, taking calculated risks with my blog this year has had huge rewards.

Some of the things I’ve tried:

  • Launching a new responsive design
    Remember the old Blog Tyrant design? It was fixed width and very outdated. But because a lot of people liked it I took way too long to re-design it because I was worried they’d jump ship. Since launching the new responsive blog design I’ve seen subscribers dramatically increase and some ancillary benefits like better Google rankings.
  • Backing my SEO strategy
    I actually don’t take many risks with my SEO strategy (not like some people out there *cough* Glen *cough*) but with all the fear that’s going around about Penguin and Panda pinging people doing the right thing I just kind of decided to “give up” and back myself. I create great content, do guest posts, and occasionally advertise, and if Google doesn’t like something as white hat as this site then there’s not much I can do about it. I’m not going to waste time disavowing links and stuff like that – I’ll just keep trying to help people with content.
  • Asking for help
    It might not seem like much of a risk but I have always found it quite difficult to ask colleagues and friends for help with business. Mental health issues? Sure, I’ll talk about it til the cows come home. But business issues always seemed selfish. This year, however, I’ve asked a few people for big things (endorsements, guest posts spots, advice, etc.) and it has really paid off and changed my direction on a few big issues.
  • Focusing on one site vs many
    When I first got started with blogging I wanted to have many smaller sites and make money that way. Eventually I thought that I could sell those blogs once I was bored of them or wanted to move to something else. But last year I decided that that model was too difficult for more. I didn’t enjoy it and wanted to focus all my energies on the Blog Tyrant brand. So far it has been a great decision – I love my work, I get to (hopefully) help some people and it’s finally getting to the levels I’d like it at. It’s a risky set up but I hope it pays off.

These might not seem like huge risks (it’s not like I’ve invested $1m into anything) but any change to the way a successful business is running is obviously quite significant for the owner.

Let’s hope that they continue to be the right choices.

A final word on how to take more risks

I can’t emphasize enough how important it is to calculate your risks.

I really don’t want anyone to go and do something stupid as a result of reading an article on my site. That would be very bad.

Perhaps it’s best to consider this a starting point for the idea of using smart risk taking as a way to improve different aspects of your life?

There are so many good articles out there about what risk is and how to calculate it and perhaps why it’s bad for other aspects of our life as well.

At the start of this article I used the “It’ll be fun, they said” quote to make it seem like risks are a bad thing. Sometimes that is true, but often in business it’s something that we kind of have to get comfortable with if we want to go to the next level.

It’s still hard, but it is making a difference for me.

Sometimes I wonder if it’s the difference between the profitable blog and the one that flops.

Have you taken any risks?

Are you the kind of person who takes risks in life and business, or do you prefer to make things as safe and stable as possible at all times? I’d be really interested to hear what (if any…) risks the Tyrant Troops have taken so please leave a comment and let me know.

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  1. Great article, as usual! For someone who is still forming and growing a reader base (my fashion + social action blog is only about a year old), I’m sort of nervous taking risks as it could potentially mean a drop in readers or pageviews which I don’t think I could be ready to sacrifice this early in the game? For me, I view risks right now to be more of posting at different times of the day/different days, titles, orientation of the first photo in a post (I didn’t realize it was important!), etc. Any advice on how to efficiently take baby risks? Thanks!

    1. I think with that kind of stuff, in my experience anyway, readers are a lot more forgiving than you’d imagine. If they like your blog they’ll be happy to see you change things up just to test it out.

      You could always do a post about risk taking and just let them know that you’ll be trying some new things and to let you know if they really hate it. Feel free to mention this article. 😉

      1. Hm, I guess you’re right–maybe making a little heads-up post (haha not forgetting to mention this post, of course! c; ) might be a good idea–thank you! 🙂

  2. Tiru pradyumna on November 13, 2014

    After reading your posts i understood the difference between Self-hosted and other kind of websites. It inspired me to buy a domain and start a new site. It will go live Dec 1st week.

    I welcome your suggestions.
    It is a site to promote staged events(plays and dramas in specific) across a city. It is a non-profit one. I really don’t expect any returns from our partners. Is there anyway so that we can make this site earn money to sustain its expenses? And also what are the factors need to be considered to launch a non-profit site?

    1. Hmm… this is a tricky one as I’ve never launched a not for profit website. Perhaps one of the Tyrant Troops might have some answers for you?

      1. Tiru pradyumna on November 13, 2014

        Thanks. Will be expecting troops here

        1. Scott Kindred on November 13, 2014


          One suggestion is to look for local sponsors to defray that cost of the website. Get sponsors for the stage performances as well as exploring ad sales to local businesses who provide services that are related to the genre or location of your performances.

          You could also try making some money with your website through Google AdWords or affiliate sales.

          Donations are another way a lot of non-profits try to reduce costs. Have a place on your website where people can make an online donation. PayPal is the most common way to do that and they have easy integrations for WordPress and other website platforms.

          Additionally, many non-profits can eliminate a chunk of their website expense through being a government-recognized non-profit organization. In the U.S., for example, legit non-profit organizations can get free website hosting services from commercial companies who offer special discounts to NPOs. Dreamhost is one of those companies, and there are others. Not sure if this applies to your location, but it is worth looking into as a way to reduce costs.

          1. Tiru pradyumna on November 13, 2014

            Thanks for your inputs Scott,

            First point sounds well practical in my circles. Sponsorship will be feasible in my case. Other points, i may need to try them in later stages.

            I have created a dedicated blog page as a part of my site. When we promote events of a certain troops, we ask their faculty to guest post for our blog(It is not mandatory). The concerned people have shown great enthusiasm in ‘writing for us’. Do you think is it going to help this site?


  3. Anxiety is a tough master, I know her well. Fortunately for my success, she tends to flay me forward into action rather than paralyze me with her venom.

    No one ever died of lack of sleep I tell myself.

    Risk…is a funny thing, in that most people suffer from information asymmetry and miscalculate risk. Society and our parents are also a great source of risk myth. Throw in a little confirmation bias and you end up with a very safe path with no reward. Does it make you happy? That is considered irrelevant.

    Safety is a lie. It doesn’t exist. So make the best choices but don’t be complacent and enjoy life. Life is good, there are people who’s only purpose is to print money for our governments. Let some of that be yours.

    1. Your comments never fail to entertain and motivate me, Rachelle. Never change.

      1. First off, thank you for this article/blog post Sir Ramsay!!! I do so enjoy reading them all.

        And to Rachelle … I think your comment just sparked a new found confidence within myself. I was never one to take risks (not even calculated ones), but of late I decided to take the plunge. Tough times ahead for sure (and the present state of affairs seems, well … daunting), but I still have some “fight” in me left after all. Thanks for the reminder.


        1. Love this group!

    2. InternetLocalListings on November 18, 2014

      “Safety is a lie. It doesn’t exist.”

      This is perhaps one of the most to-the-point and accurate statements ever. For many of us, we were urged to get “stable” jobs, or “reliable” jobs, meaning safe, of course. It’s not a guarantee–never was, although it’s definitely changed in today’s marketplace–and the sooner you realize that, the better. Some people are meant to do things like that. But those people don’t visit blogs like this.

      Thank you for the affirmation and motivation 🙂

  4. Tor Refsland on November 13, 2014

    Hi Ramsay,

    thanks for sharing.

    I really like the part where you are saying that taking calculated risks with your blog this year has had huge rewards.

    If you want to achieve something that you don`t already have (experience / achievement), you have to do something you haven`t done before.

    It`s all about going outside your comfort zone.

    Don`t be afraid to try new things. When you are entering unexplored terrains, it can be frightening, but it`s often well worth action.

    I do have to second that part “calculated risks”.

    No need to go all “Jack Ass” and put the physical part of yourself in actually real danger.

    I like to have an analytical approach to new goals / journeys:
    1. Do good research about the journey you are about to start
    2. Set a goal – What do you really want?
    3. Check your burning passion about reaching the goal (this will keep you going when the hard times come, and you feel like quitting)
    4. Make the plan
    5. Analyze the cost (time, resources, money) vs. end result
    6. Decide if you are actually going through with it or not

    And here is the key: if you decide to follow through with the plan, and actually go for the goal. You have to program your mind to do the necessary tasks, no matter what – whether you feel like it or not.

    It`s all about mindset and conditioning yourself to do, what most people don`t.

    The experts say that the only difference between a successful person and one who isn`t, is that the successful person is willing to do what the unsuccessful person doesn`t like to do.

    And here is the real kicker: the successful person doesn`t like to the tasks either, but he does it ANYWAY.

    In the last 6 years I`ve been expanding my comfort zone continuously.

    Some of the rewards I`ve achieved:
    -Tripled the income within 5 years
    -Mentored others
    -Has spoken on stage in front of 3000 people in Nice
    -Met my girlfriend and future wife
    -Earned into the six figures
    – Been a part of several business ventures
    -Lost 13 pounds in 29 days without starving

    I know that my life before I expanded my comfort zone vs. after – is like night and day…

    Doing things you have never done before is always a bit scary. But that is a good thing, just do your research and follow my plan above, and you will be fine.

    Join me in expanding the comfort zone, so you can achieve more and be the person you truly deserve to become.

    Tor Refsland

    1. Dude! Is this an original comment?

      1. Tor Refsland on November 13, 2014

        Yes, made specifically to you 🙂

        1. Thanks so much mate. I really appreciate the time that must have taken you to write that. Absolutely amazing.

  5. Susan O'Dea on November 13, 2014

    Hi Ramsay,

    When your email landed in my inbox, I clicked immediately to read your article.

    Over the years I have taken many risks…but I never knew they were risky at the time. I was following people’s advice who I trusted…LOL…I don’t follow them anymore as it hurt some of my sites badly and me emotionally.

    Now that I have been online for many years I steer clear of all risky ventures. That doesn’t mean I don’t take some risks in areas of my marketing, I just mean I don’t take risks that could hurt my business rankings or lose any Google love.

    I remind myself of “The Tortoise and The Hare” story. 🙂 I was once a hare…now I’m happy I chose to be the tortoise. 😉

    1. I’d be really curious to now what risky things you tried that you weren’t happy with…?

      1. Susan O'Dea on November 13, 2014

        Where do I start without sounding like I’m pointing the finger? Let me just say I spent $20,000 on a sure thing, (approx. 7 years ago) which turned out to be a huge scam…and the person is well respected.

        That was the first and the risk was money invested…then the risks were smaller financially (approx. $2000 month) but the damage greater.

        Today I take no financial risks in business, market only with white hat strategies and the rewards are greater than any ‘successful’ risky business venture.

        1. Wow I’m really sorry to hear that. $20,000 is a big investment for it to go badly.

          1. Susan O'Dea on November 13, 2014

            Just one of life’s lessons…and learned from it.

  6. Scott Kindred on November 13, 2014

    A quote from you in this post: “I love my work, I get to (hopefully) help some people and it’s finally getting to the levels I’d like it at. It’s a risky set up but I hope it pays off.”

    I really think that sums it up. Because if we (meaning me) are not helping people, then all the other stuff doesn’t matter. I admire your long-standing philosophy about that, having watched it in action for a few years now and having see you selflessly help an number us us who hang around here.

    My gig is pretty commonplace – web design, social media & SEO. I mean, who *doesn’t* do that these days. But what makes the difference is the people I get to help in my little slice of the world. Doing abut 80% of my work with non-profits and faith-based organizations; nice payoff, given the risk.

    1. Hey Scott.

      I really appreciate you saying that. I always try my best. But it’s pretty easy with awesome people like yourself who keep reading and commenting.

      I think SEO and web design can have a HUGE impact on someone’s life if you do it well. Helping a small business make enough to get by, or make a bit more online is a really big deal to that family.

  7. Starting our blog was a risk in the 1st place since I really had no idea what I was doing, whether I would be any good at it and whether I would enjoy it. I knew very little about the business but I knew what I wanted to say and where I want our business to go. I found out that not only do I like doing this – I love it.

    Not knowing all of the rules was possibly a good thing and my knowledge of pandas and penguins stops at them being cute. A reality however is that you need to establish a solid base of readers and people interested in what you have to say before you can take more risks. This means a bit of a conservative approach until this is established… I think.

    Thanks Ramsay, I really enjoy reading your posts and need to re-read about building the email lists, which is on my to do list but keeps going to the bottom as it is too hard. I am pleased you have said to ask for help when you need it. Can you do my email list for me, please? ☺

    1. Ha ha. I could maybe point you to some resources. 😉

  8. Hey,

    thanks for the great post. I decided to go a similar way, stop doing niche sites and focus on one big blog.

    I launched it seven days ago and had some pillar content prepared – it paid of and already got over 3000 uniques with a peak day of 800.

    All the best to you and I hope it works for both of us 🙂

    1. Legendary! That’s awesome to hear.

  9. Hi Ramsey

    It is a year since I got my domain name and now I have set up my parenting site, believeability.org.uk At the moment all to do with my site is a risk as it’s all still new to me, and I still have no subscribers! So making an ebook, a taster course, and blog posts are done with risk of being imperfect and not up to standard because if I didn’t allow that risk I wouldn’t do any of it.
    Your site has been a great help with many things though so thank you. Any further advise is great fully received.

    1. It sounds like your on track for something great. Just make sure you figure out how to make your blog distinctive, and then work on highly useful content that solves practical problems.

      1. Thanks x

  10. Good advice, but it gets harder to implement as you get older. I had a huge appetite for risk early on, which resulted in some wins but the losses hurt too.

    Unfortunately we tend to remember the bad far more than the good over time, but a well calculated risk is required every once and a while.

    Nothing ventured, nothing gained 😉

    1. Yeah it is harder – especially as you get more responsibilities as you get older as well. How’s life for you mate?

      1. Going well, gotta grab some Chinese with you to catch up though. Sneak something in before Christmas?

  11. Ramsey – I really need to take more risks with my blog in the upcoming year – I need to work on the theme design and much more. I love your new design here – so clean! Thanks for the inspiration here – I love your quote how the actual event is never as bad as we worry about it beforehand – so very true! I try to remember that often if I start to worry about something, it can be such a waste of time and especially energy!

    1. Yeah it’s a hard one to remember, I struggle with worry sometimes too. But it really doesn’t help anything, ever.

  12. Time and time again, the result of taking a risk has been…

    “dang, I should have done that sooner.”

    1. Well.Said.

  13. Taking risks is one way to find great feedback. When you do something that is out of your norm it reflects in your writing.

    Giving a “heads up” to your audience is always helpful because you are letting your readers know there is a change coming. Your readers in turn will let you know what they like (or don’t like) if you ask.

    I took a risk this year. I finally decided to start a blog about my personal life experiences. Its not much right now I am still learning how to navigate WordPress, plugins and services that are useful for running a website. I will keep learning and growing so hopefully one day I can earn a living from this lifestyle.

    I always look forward to your posts, they bring insight and experience to a newbie. Thanks

    1. Thanks so much Nick. I’m glad you’re enjoying them. Anything I can ever do or write about just let me know.

  14. Ryan Biddulph on November 14, 2014

    Hi Ramsay,

    I took every one of your risks and love your mindset. I see risk taking as giving yourself opportunities. A few different words but man it made me feel better knowing I gave myself opportunities to be free by moving in new directions.

    I trashed my old blog. 3400 posts and all. Blogging from Paradise was born. I gave myself the opportunity to speak at NYU about how to blog and I gave myself the opportunity to be endorsed twice by Chris Brogan, and once by Yaro Starak.

    What a cool shift, right?

    I took exciting opportunities by changing the words I used, and by changing my feelings, about risk-taking.

    As a guy who’s been a broke security officer, and who’s rented villas in Bali for months, the villa renting guy understands that the broke guy feared taking risks, while the villa renting guy was excited to seize opportunities.

    Change this tipping point and you’ll take more risks than you ever dreamed of: become more hungry to be free than you fear doing uncomfortable stuff. As your freedom momentum builds you’ll take risks, or, give yourself opportunities, as a force of habit.

    Right Now, I’ve giving away hundreds of my eBooks for free, in exchange for reviews. Old me said risk, new me says, it’s an abundant act, and gives me tons of reviews, and spreads the word so more are inspired to blog from paradise, and of course, reviews *do* mean more sales too. Calculated risk indeed hehehe….thanks Ramsay for speaking the risk truth here today.


  15. Rodney Robinson on November 15, 2014

    Thanks for sharing your risks, Ramsay. This may not sound huge to some, but i understand. The subtle adjustments can seem the most risky to the person making the changes. You have a routine, a comfort zone, a way of doing things. And those are the same risks that I have begun to take. I recently re-branded my blog with a small pivot from only marketing-related content to business/leadership/best practices. Did this with little thought and much confidence and have seen broader interest and can create more practical and useful content for my target audience. In a way, although we can fear them, we love risks!

  16. Kerry Russell on November 15, 2014

    Hi Ramsey.

    As many of my mentors have taught me, we don’t achieve anything if we don’t step out of our comfort zone, and it’s so true…

    But for me, that’s easier said than done. I do have an anxiety disorder, and that makes risk taking a bigger challenge than it is for most people.

    However, just recently I plucked up the courage to re-brand my business after 12 months of working 16 hour days growing my old blog – basically starting from scratch.

    As someone who was struggling online for almost 3 years prior to building a successful blog, it was a big risk to take after finally achieving success and earning a decent income online.

    The bad news; I lost some of my audience because of the re-brand.

    The good news; I’ve recently built a referral relationship with Yaro Starak, who is recommending me as his ‘go to gal’ for WordPress support and small jobs in his upcoming product launch this January.

    Whatever risks we take, they all come with pros and cons. Like you said, we just have to calculate the risks we take and make sure we are well informed before doing anything we may regret.

    Congrats on stepping outside your comfort zone btw. Been reading your content for some time now and love what I see. Keep up the good work.


  17. Very much like the emphasis in this article about the balance of risk taking. That’s what it’s about.

    Currently in the position of trying to turnaround my blog with some “risky” content, it may ostracise me from the industry but I think it’s worth it.

    Keep up the great posts.


  18. I’m quite cautious but also don’t want to avoid taking risks altogether as often it’s a good thing. Lets face it setting up your own business is one of the biggest risks you’ll ever take. I’ve found the best thing is to not do anything in haste, spend a few weeks, or months if needs be thinking through the risk you are considering taking and all the potential implications, speak to friends and get their opinions too and make sure you have weighed it up fully before jumping in. The biggest mistakes tend to be made by those who rush into it, taking risks doesn’t mean being stupid.

  19. I’m afraid of taking risks when it comes to my family, But for business and blogging, I often take risks and most of the time the result impresses me. However, A well-written blog post. Thumbs Up 🙂

  20. Ramsay,

    This risk-taking mindset is not easy to get used to. Growing up, my parents (both engineers) hammered a “don’t take risks” philosophy into my head.

    This philosophy has really helped me with my finances as an adult, but now that I’m venturing into the entrepreneurial world, I think it’s hindering me. I too, try to make things too close to perfect before unleashing them to the world.

    One thing I’m kind of battling with right now is the idea of taking on debt to advance a business. I just don’t want to take on debt, period, but I wonder how many successful entrepreneurs can actually thrive with a no debt philosophy?


  21. They say that 90% of things you fear never happen. I guess this can also be applied to taking risks. My mother always used to say those who do not take risks never win.

  22. Andrew Park on November 20, 2014

    Very common trap for bloggers to just look for conventional wisdom and color carefully within the lines…good reality check here to help challenge people to exit the comfort zone and try something new.

  23. Thanks for the insight Ramsay.

    Everyone of us have aspirations to achieve in life, but you can’t reach your dreams if you play safe and static. We learned from risks and those lessons may bring us to reach your goal. There’s nothing wrong if you take a risks in business, what matters most is you are prepared for all the possible consequences. Always have a plan B.

  24. Rodney Robinson on November 22, 2014

    Well-calculated risks really are not risks if they are well-calculated. It’s all about managing risks. “Risk-averse” people, like myself, do not necessarily avoid risks…they manage them. This works for me and may work for others who use risk aversion as an excuse or reason to believe they cannot take risks. (I will probably make a post about this on my own blog – Thanks for the inspiration, Ramsay!)

  25. Hi Ramsay,

    I do believe that most of the businessmen are risk takers, like me. Because you can’t achieve the things you want in life if you don’t jump off from your comfort zone. Over the years, I have taken many risks but the lessons I learned from my experience keeps me strong.

    In business, I see to it that I have hired the best team whom I trusted before I take the risk. There is always a backup plan.


  26. The Essential Guide to Writing Potent Blog Posts | The Creative Copywriter. on November 25, 2014

    […] Ramsay Taplin’s stuff is a prime example. Gregory Ciotti’s flow is darn good too. I also like how James Charthand mixes up her paragraph length. And of course, hypnotic copywriting legend, Joe Vitale, always gets it spot on. […]

  27. Hi Ramsay,

    I share some of your same feelings about taking risks. The thing that’s helpful for me to remember is that standing still or not changing anything is also a risk! There are no guarantees either way, so you really can’t be 100% confident that making no changes at all is going to continue being successful indefinitely.

    So making a change and choosing not to change are both risky in my opinion.

  28. Hi Ramsay,

    Great blog post! We all have to take risks in life as everyday is a risk. We have to take risks in both life and business. For example, we take a big risk when we get out of bed every morning and going out to work or where ever else we go. We could end up dying on the way. This example is slightly extreme but it’s still a big risk.

    You have made some good points in this blog post like always and your articles are always thought provoking.

    BTW your theme is awesome!



  29. Alex Periera on December 10, 2014

    I remember some body saying that “not taking risk is the biggest risk” and with experience I have come to agree with this quote.

  30. Ben Robison on December 11, 2014

    I’ve always been risk averse. Even the development of my blog is an attempt to diversify my risk by having another source of income besides my day job. But this idea of smart risk taking is something I can get behind. I need to think about what steps I can take.

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