21 Experts Reveal Their Biggest Risk That Paid Off

By: | Updated: December 10, 2020

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“And the day came when the risk to remain tight in a bud was more painful than the risk it took to blossom.” – Anais Nin

I asked 21 top bloggers this question: “What’s the biggest risk you’ve taken that you feel has paid off?”

Jon Morrow of Boost Blog Traffic

Moving to Mexico in the middle of a drug war with no friends, no money, and no way to leave if things got bad. My entire family thought I was insane. My poor 80-year-old grandmother even drove across the state to come tell me goodbye, like I was going to die.

And I could have. I really could have.

Instead though, I built a multimillion dollar business and came back to the United States, one of the only severely disabled people in history to become entirely self-sufficient. It was a huge gamble, yes, but the payoff was enormous. 

Ramsay Taplin of Blog Tyrant 

When I first started blogging I worked as a cleaner from 6 am to 10 am every morning. This allowed me to make enough money to pay the bills, and then gave me enough time to come home and work on building up my web assets. Letting go of that job, however much I hated it, was a huge risk for me at the time. It was a safety net I really thought I needed. It was around that time that I also dropped out of college (with one semester to go…) in order to capitalize on my blogging opportunities. It was scary and everyone thought it was a bad idea, but I’m now running my own business and earning probably more than I ever could with my degree.

Donna Moritz of Socially Sorted

Don’t be afraid to Pivot Your Blog when the Time is Right The biggest risk I made was in pivoting my blog. It’s funny, because now I see the results, I can say that it probably wasn’t a “risk” but a natural decision that was necessary. Pivoting your blog can be a BIG decision when you are finding your feet with blog direction. I realized in the first year that the posts I was writing about that were resonating the most with readers were the posts about visual content, so I switched to writing more about these. I also enjoyed writing about these posts so it was an easy decision. Watch for spikes in shares and comments on your own blog – what lights up your readers that matches up with what you enjoy writing about? Try doing more of that. For me the risk was worth it – after I pivoted my blog I quickly increased readers, subscribers, and won major blogging awards like Best Business Blog in Australia in 2014 and Top 10 Social Media Blog for Social Media Examiner in 2015. I wasn’t blogging any more frequently, but I was blogging about a topic that resonated – with me and with readers. I would also add that pivoting does not need to happen quickly and you don’t need to “niche” your blog straight away. Sure, if you have a topic or focus that just seem right, start out that way, but there is no shame in pivoting to be more general (if your niche is not as interesting to readers as you thought it would be) or pivoting to niche (if you find that you are getting great results about a particular subject like I was). Give yourself time to watch and test – sometimes it takes a while to find your blog voice and to find your “tribe” of people, your ideal audience that love to read what you love to write about.For more advice on how to ‘find the sparks’ that will help you pivot your content, I highly recommend you read this post and watch this video. Darren Rowse was the man who made me realize that those sparks were worth pursuing, after I saw him give a similar presentation at Problogger Event in Australia, 2012. This is a must-watch video for all bloggers. 

Pauline Cabrera of TwelveSkip

Biggest risk? Hmmm, that would be investing time on something without knowing whether it will work out or not.

For example, in the first year of my blogging, I invested so much time in Twelveskip without getting that much in return. It’s like I was working full-time for free. I kept telling myself to have fun and be passionate because I believed one day all these would pay off. I spent most of my time learning, experimenting, networking and creating content. I was inspired by those people who started from nothing (like Michelle Phan) and became really successful because they are passionate about what they do. If they can do it, why can’t I, right?

Now I’ve been happy with the level of engagement I’ve got. I love how I actually make a living from blogging. It took me a year and a half to figure all out but I never felt like it’s work. I’ve loved every bit of it.

 Jenna Dalton of JennaDalton.com

One of the biggest risks I’ve taken so far in my business is when I volunteered to be in front of 30,000+ people and have my business dissected. I applied to be part of the audience for the CreativeLive taping of Michael Port’s Book Yourself Solid 3-day workshop and I got accepted. Being an introvert, it was a terrifying thought to be in front of thousands of people and have someone tell me what I was doing wrong. It was even more terrifying because I was at a crossroads – I had decided I didn’t want to focus on personal training and nutrition coaching anymore, but I was still figuring out the exact direction I wanted to move my business in.The morning of the first day of filming I felt like I was going to throw up. I almost chickened out. I wanted to fake being sick and just stay in my hotel room. But I went. And during those 3 days Michael became a powerful mentor for me. He still is. I’m so glad I got over myself and just went for it because I can say with absolute confidence that my business is where it is today because I said yes to that experience (even though it scared the pants off me).

Dennis Seymour of LeapFroggr 

In this early stage of my blogging journey on LeapFroggr.com, I think the biggest thing so far was that I decided to publish once a month, instead of once a week, because of my crazy schedule. I would often miss my deadlines and it would just lead to more depressing thoughts and as you know, that hurts a blogger’s productivity very much.This way, I can maintain the quality of the posts, promote each one for a longer period, have time to create unique content for my email subscribers that builds up to the next post and it gives me enough time to create guest posts on other sites. Has it paid off? So far, it has given me time to talk to my email list, build new connections and make friends like you, Sue.If this keeps up, I’ll be able to have some extra time to actually do something with my personal blog by the 2nd half of the year and probably venture into podcasting a little later after that. 

 Adam Connell of Blogging Wizard

The biggest risk I’ve taken was when I left my job to focus on blogging full-time.

This was a serious financial risk. As with most forms of online income – there are no guarantees. But, I felt the risk was worth taking in order to scale my blog.

6-7 months later and I’ve grown my income by 500% which is beyond all my expectations. There were a few moments where I had serious doubts but I’ve always believed that anything can be achieved if we put our minds to it. 

Tor Refsland of Time Management Chef

In the past I was running a few businesses, while having a full-time corporate job. That wouldn’t have been possible, if I hadn’t cracked the code on time management, which helped me increase my productivity by 200%. Even though I was doing quite well in terms of income, I knew that my energy and time was spread out on too many projects. Success is all about goal setting, time management, productivity and focus.

My biggest risk was when I decided to leave my six-figure corporate job and pull the plug on all my other businesses, in order to follow my true passion – to found Time Management Chef, where I help online entrepreneurs free up more time, so they can focus on what they really love.

Yaro Starak of Entrepreneurs-Journey

The biggest risk I have ever taken was the decision to pursue entrepreneurship in the first place and avoid any kind of full-time job. That meant I had to be responsible for my income directly and not rely on someone else to pay me a salary. If things didn’t work out I could still be living with my parents now, which would not be so great at 35 years old!I feel it definitely paid off of course, given the kind of lifestyle I’ve been able to live for the past 15 years. I’ve been able to travel the world, construct my days how I want to, and earn much more money than most people ever make working a job.

Andrea “Dre” Beltrami of The Branded Solopreneur

No question, the biggest risk I’ve taken is rebranding my business from scratch. In fact, it was a HUGE gamble and down right terrifying, but I knew it was the right choice for me. The unfortunate truth is, I spent almost 2 years building a brand around a niche I had very little interest in and a persona I manufactured in an effort to ‘be professional’. Ultimately, I decided I had to ditch it all and start fresh. Something others told me I was a fool for doing.After 3 months of soul-searching and rebranding I proudly launched The Branded Solopreneur. This new and improved brand is 110% unapologetically true to my style, personality, talents and passions. It’s this seamless personal alignment with my business that I credit with allowing me to surpass the success that took 2 years in my last brand in just a couple of months after launching my new brand. Taking a chance on myself and following my intuition has been the most rewarding risk I’ve ever taken, which makes reaching each need level of success I attain that much sweeter. 

John Meese of JohnMeese.me

The biggest risk I’ve taken that has paid off?I walked away from a job without another job waiting. I wasn’t comfortable with some financial practices in the non-profit I worked for, so I resigned without a clue where I’d be going next—within weeks, I had four job offers to choose from, all better. That was a lesson in trust falls, for sure!

Stuart Walker of Niche Hacks

I used to make a full-time living from low risk online casino bonuses and sports betting. That was great for a few years then started to get more difficult so the money was drying up. I took what was left of my cash and went and traveled around South America for 6 months. Came back broke and had to get a mind numbing office job.After a few months I’d saved some cash up and decided to quit and go travel in South East Asia for 6 months. I decided that whilst out there I’d figure out some sort of way to make money online but I had no real idea how I was going to do it as “internet marketing” didn’t mean a thing to me then. Suffice to say because I had no plan or idea what I was going to do I never got round to doing anything and was resigned to the fact I’d be going home broke and have to find a job. Near the end of the trip I met a guy who was doing SEO and affiliate marketing and he inspired me to give internet marketing a try. I went back home, broke again, but determined to make it work.Instead of looking for a job I decided to dedicate myself to online marketing determined I would make it work, so I started using my overdrafts and credit cards to fund it. It took a while (well over a year to even begin to see any consistent income) and there were lots of points where I thought maybe online marketing wasn’t for me and I would have to get a job but I was persistent and eventually it worked.It was pretty risky because if it didn’t work I’d spent a year + the 6 months before when I was traveling out of a job and would probably struggle to explain to potential employers what I’d been doing that time (I can’t imagine them being impressed by me messing around on the internet), I’d be broke and in debt, and in a worse situation than before.Everyone I knew during that time discouraged me and told me I had to get a job, it wasn’t possible to make cash online and so on, but I knew it was possible and just didn’t want to give up on that dream.Paid of now. Have a generous income the internet, an online business, can travel as I please, am location independent and live abroad. Glad I took the risk.

Brian Lee of Genius Types

The risk I took was foregoing the security of a great career path, the foundation of which I had built over three years working there. At the trajectory I was on when I left, I most likely would have been in an executive position today.Instead, I chose to travel the world, work in the film industry, start a blog, and eventually use my unique set of skills in my own business as a content marketer for myself and clients.The path wasn’t easy, and there were times where I felt I’d made the wrong decision. Despite the struggle, I wouldn’t trade it for the world. Today, I enjoy a level of freedom and control over my life that I would not have been able to achieve on the other path.As an unexpected bonus, my set of skills is very hard to replicate. Therefore, my earning potential is virtually unlimited.If someone were to ask me if I recommend this path to others, I would say that it’s not for everyone. The sacrifices were great. If I had other people relying on my income when I left the security of my job, it would have been the wrong decision.But, If you have carefully weighed the risks, are willing to pay the price, have the talent, and get a little lucky along the way, the reward can be worth the risk.

Jerry Lowe of Web Hosting Secrets Revealed

14 months after WebHostingSecretRevealed.com got slapped by Google Penguin, I decided to shift everything to a new domain for better prospects. The .com site was one of Majestic Million (it’s still ranking 130,755 today) and my main income source back then. Leaving the site behind meant I had to rebuild everything from scratch with zero traffic and income. I was literally losing thousands of dollar per month in content and our new tool (WHSR Uptime Monitor).

 Luckily, it turns out to be a right call.

Today, the new site WebHostingSecretRevealed.net is better than the old ones in many ways. We are now less dependent on Google Search traffic; the site has a better brand recognition, get shared 100x more often on social media, and personally I have much better sleep at night not worrying of another Google penalty.

Sylviane Nuccio of SylvianeNuccio.com

The biggest blogging/business risk that I’ve taken, could easily be the one I took four months ago, when I decided to merge my 3 blogs/niches together under the same roof.

Why was it a risk?

Because most of the bloggers I know were advising me not to do this, giving me all the reasons why it would be a huge mistake. After all, it’s hard to put 3 niches under one domain name. Isn’t it?

But all I needed to hear is that while difficult, it was POSSIBLE.

Four months later, looking back at my blog, everything is on the rise.

  • More traffic – That traffic curve keeps going up steadily every month since December.
  • More interactions on each post – 50+ comments on a bad week to 100+ on a good one.
  • More motivation to write great content – Having only one blog to manage is more motivating for content quality.
  • More motivation to create original and costumed images for each post – This helps me developing my brand through images at a whole new level.
  • More motivation to promote my posts – Feeling good about my blog gives me more energy to promote it.

My blog and I are getting noticed. I can see that by the increase in guest post requests, post contributions and other interviews that I am getting these days.

The merging of my 3 blogs under one roof was a success. The risk paid off.

Dev Sharma of WPKube

I think the biggest risk I’ve taken is selling my business blog to focus on a niche topic. Four years ago, I sold my main business blog to focus on WordPress niche. It was my main income source at that time and selling the site meant, I
would have to start from scratch.

Now that I look back, it looks like shifting my focus to WordPress niche (with WPKube) was a right call.

Today, I have a good presence in the WordPress community, featured on many authority sites, an amazing team of writers and bloggers, and above all, have been able to help a lot of beginner WordPress users.

Neil of Blogician

Biggest risk? Got to be trying my hand at grey/blackhat SEO. I have a relatively new blog in the relationship niche. Great content, well optimized – but still crappy unrelated sites were outranking me for the main keywords. A quick backlink check showed huge number of blackhat backlinks. Frankly speaking, Google’s algorithm was not doing a good job. So, I decided to give it a helping hand (not mentioning the blog for obvious reasons).

I ordered 60 do-follow comments on pages having valid PR. Received -20 penalty! Ouch! Should have gone slower. Next up: Guest post on PR5 blog (basically it’s for selling guest posts only). I wrote a 1200 word article and used a contextual link (in first paragraph). I also used an image backlink with keyword in the alt tag. Then I ordered 300 Plus ones for my homepage, drip fed over a week. Voila! My blog jumped to #2 from #10 for Keyword 1. For another high competition keyword, my blog reached #16 from #130.

The results were completely unexpected. I was just doing this as an experiment. I was just hoping to avoid a penalty. But it turned out to be a nice experience for me. My risk paid off. It has been months now and I am making a few bucks from it.

I am not encouraging you to try this for your main blog; I never try these things on Blogician. But for niche blogs, you can give it a go. After all, if your blog is being outranked by crappy sites, why would it be wrong to fix it? You are just showing Googlebot the right direction! What do you think?

Donna Merrill of Donna Merrill Tribe

I think the biggest risk I took was when I spent a substantial amount of money to get one-on-one coaching for product creation and marketing. 

At the time, I thought that maybe I was spending too much money just for “some advice.” 

But it changed my whole perspective and my business has soared since. It was a big financial risk at the time, but in retrospect, I’m sure glad I did it. 

Of course, I had to take action on what they taught me, but without their direction I would have taken action on things that got me nowhere.

Now, I use coaching each step of the way, because I’m convinced it’s really the only way to move your business forward.

Instead of thinking of it as a risk, I now consider coaching to be an essential part of my business budget.

Lorraine Reguly of Wording Well

Living life to the fullest often involves taking risks, and being a blogger is no exception. The funny thing about blogging and being a blogger who takes risks is that the outcomes can be difficult to predict and are frequently not what we expect.Sometimes success can occur accidentally, too, putting your name on the map when you least expect it.Take the fourth blog post I ever wrote, for example, about my experience with downloading malware and the measures I took to rid my brand-new laptop computer of it. It hit the first page of Google Search, making my blog “discoverable” by those who were in need of the solution I found.Finding the solution, however, required me to take a huge risk: to put my faith and trust in a total stranger, and believe that he knew what he was talking about. I mean, I had *just* trusted a reputable site with a PageRank of 8, and all I got was a piece of free software that ended up being malware. My entire belief system had been shattered, so it was difficult to trust anyone or anything. However, I knew I had to act, and I had to act fast. I had no choice; I had to remove the crap that was put on my computer. This involved downloading a special program to remove the culprit.Fortunately, it worked. I successfully ran the program and rid my laptop of it’s “infection.”Then I immediately wrote about my experience. I wanted the world to know that the VisualBee Toolbar is malware. I didn’t want others to go through the agony I endured. Because I’m a teacher, it’s my nature to be helpful.Writing honestly about each step I took caused Google to notice my free little blog. It also helped my credibility as a new blogger. It fueled Google to pay attention to my future posts, too. In under a year, I had achieved a PageRank of 2. Not too bad for free blog on WordPress.com! ?Because many more of my posts ended up ranking on the first page of Google Search (plus a few other reasons), I decided to get my own, hosted site. After doing extensive research on hosts, domain names, niches, etc., Wording Well was born.During my first year of blogging, I began working as a freelance writer and editor, but after becoming a seasoned blogger and then published author, I added other various web-related and publishing services to my list. Now Wording Well is a certified, registered business, and I’m living life to the fullest — because I took risks (and still take them), and because they have paid off. 

Matt Banner of On Blast Blog

The biggest risk I’ve taken that has paid off is deciding to get started with my online business. Putting that first pen to paper or that first finger to your keyboard is probably one of the most difficult things to accomplish. No, the biggest risk is not about developing a unique link building strategy or adding elements within your content to increase engagement.

The decisions to reshape your life and harness your passion towards starting a blog is the highest hurdle you’ll face. Starting a blog is sort of like jumping out of a plane. As you approach the open door at 18,000ft in the air, you’re incredibly apprehensive about doing this and you’re certainly rethinking everything. However, you know that you’re with a trained professional and if you follow the best practices and guidelines set out for you, you know you’ll make it to the ground safely. 

In blogging, most people are too afraid to take that first step. Making that decision to take a risk and start that blog you’ve meant to get up for years now is half the battle.

Kevin Duncan of Be A Better Blogger

The January during my senior year of college, I signed a contract to begin work as a high school teacher immediately after graduating in August. The only problem was I wasn’t due to graduate in August. I had four semesters worth of credits to complete, and only two semesters to complete them.Crazy? Yes. A huge risk? Absolutely. So why did I do it? Because I’m not afraid to bet on me. The most successful bloggers — nay, the most successful individuals — aren’t afraid to bet on themselves.Want to succeed? Start betting on yourself. 

Amy Lynn Andrews of AmyLynnAndrews.com

The biggest risk I’ve taken that has paid off is moving most of my content sharing from my blog to a weekly newsletter called The Useletter®. A “traditional” blog format in my niche (social media, blogging, making money online, etc.) is not ideal because information in this space changes so quickly. What I post today often becomes irrelevant later. I don’t like the idea of readers visiting my site and finding old posts with tips that worked a few months or years ago. And for me, keeping hundreds of posts updated and accurate became completely overwhelming.Touching base with subscribers via email each week allows me to share useful and current information in an easy-to-digest format.What’s the biggest business risk you have taken? Share it with us in the comments.

by Brett Helling
Brett has been starting, growing, and monetizing websites since 2014. While in college, he began to learn about digital marketing. After graduating, he continued to build a diverse portfolio of websites while working a full time job. After years of building the portfolio on the side, he made the jump to run his websites full time.

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