Getting started in the online was a bit tough for me.
It was 2009 or so, and all of my friends already had nice jobs and paychecks, while I was still sitting in my mom’s apartment, trying to figure things out on my own and find my place among my online mentors.
I carefully analyzed every piece of online business advice I could find and dived into almost every “next big thing” tactic that the gurus were trying to sell.
My results? Few and far between. I was making next to nothing, and if it hadn’t been for my mom who was very understanding, well, life would have been difficult for me.
Obviously and not surprisingly, I wasn’t confident at all about what I was doing.
I started thinking that maybe I don’t have what it takes, that maybe I should abandon the web, put together a CV and send it out to a couple of places, so maybe I could catch up to my friends and secure myself a nice shiny job too.
But for some reason I decided to keep going.
I probably had some internal resistance telling me that “a job” wasn’t the right path for me or something.
Along the way, I stumbled upon Sylvester Stallone’s story. It taught me two things: (1) my situation was, in fact, nowhere near tough yet, and (2) failure is just a step towards success .
I can’t explain why this particular story resonated so well with me, but it helped me regain my confidence and stop worrying about all the small and big failures I was experiencing. I knew that if I dedicated myself to doing something for long enough, eventually it would pay off.
And it has.
However. Looking back, I can honestly say that I spent way too much time running on willpower alone instead of having the right tools and mindset in place. And although it has worked for me, this can’t be the optimal way of finding your confidence.
Relying on luck is never a good strategy, and you can easily run out of your willpower much sooner than you’ll find any success.
Therefore, what’s a better solution? And is there a road-map to confidence when running an online business?
I believe there is, and that we don’t have to be wandering in the dark endlessly until successful.
So this brings me to the actual topic of this whole blog – finding confidence when running an online business.
I’m aware that I can’t give you a road-map to confidence all on my own. It’s way beyond me. After all, I’m just one guy, and no matter what I say, it will still be just one guy’s perspective.
That’s why I reached out to 13 generous experts from various niches and asked them specific questions on the topic.
Before we start, let me just be honest for a minute and say that I’ve gained an incredible amount of insights on entrepreneurship and finding confidence when going through these answers and preparing them for publication. I am very happy to be able to deliver this resource to you, and I’m also more than certain that you will get just as much value out of it as I did!
Let’s welcome the experts:
John Lee Dumas
Jaime Tardy
David Risley
Yaro Starak
Danny Iny
Cliff Ravenscraft
Natalie Sisson
Bogdan Condurache
Ruben Gamez
Demian Farnworth
Adam Connell
Mike McDerment
Bamidele Onibalusi
The road to becoming a confident online entrepreneur
Step #1: Finding the right mentors
Some people say that getting business advice from our friends or family isn’t the best of ideas (unless they are entrepreneurs). However, when we’re just starting out building our “thing,” it is rather difficult to find knowledgeable people who would invest some trust in us and share valuable information (on top of the cliche “create quality content”).
How to find people worth paying attention to? People who can give us this much needed confidence boost, who will get us going and motivate us to take action. And what’s probably even more important, how to get them to pay attention to us? Can they really have that much impact on our confidence and therefore our businesses?
Jaime Tardy Finding a mentor has been HUGE in my life.
I was constantly on the lookout for people that were where I wanted to be.
I would do whatever I could to reach out, talk to, seem eager and know how much I valued and appreciated them.
One of the biggest problems mentors have (as told to me by many millionaires!) is that they give advice, but then the person listening doesn’t DO the advice.
One of the best ways to get them to pay attention to you is to DO what they say!
And then tell them you did it, and how much of an impact it made.
And yes – they can have a HUGE impact on confidence. My first mentor made me cold call 50 people a day. He was like – you’ll get used to it! And I would never have pushed myself that much because it seemed too scary. He changed my life!
Bamidele Onibalusi
I think the best way to start is by quoting the bible verse that says “By their fruits you will know them.”
I believe this is critical, because I recently ventured into fish farming here in Nigeria and quickly realized that success in the business mainly has to do with who you learn from; various people have various “secrets” to success, and the failure rate is generally high, but why I really followed my teacher was because of the results he is getting; he has the biggest fishes and makes the highest profit of everybody else I know (sometimes his profit is up to 150% in 6 months).
Follow your mentors based on the results they are getting
However, most of the others who are very opinionated about “what works” and what doesn’t are barely getting results; they have really small fishes, profit margin is low if there is any, etc.
Determining who is worth paying attention to is simple; look for someone getting the kind of results you are getting, and follow the person until you are getting your desired results.
Once you’ve determined the leaders you want to follow, the most effective way to get them to pay attention to you is to …
reveal your PASSION to them
If you are really passionate to succeed, you will give it everything it takes and you won’t care how difficult or ineffective it seems. Leaders see that, and they are ready to support those who have that kind of passion; look for tips they share freely online, passionately utilize these tips to get results, and showcase your results to them, letting them know it is thanks to them, and tell them you will like to learn from them in a closer way. This can be very effective!
Getting advice and support from the right people can impact your confidence as well as ability to succeed; sometimes, it is often the no. 1 most important factor.
Step #2: Making your vision clear
The way I see it, problems with confidence are often connected to our lack of clear vision as for what we want to achieve (and how we want to achieve it). In other words, because we don’t have the right goals set, it’s not clear to us what to do next. This prevents us from getting stuff done and building our confidence along the way.
How to go about setting the right goals? How can someone get over the initial vague idea of “think about what you really want to achieve and make it your goal?” How to be specific and create goals that motivate rather than discourage?
David Risley The best way to get those goals is to break it down like a hierarchy.
Start out with with the big, grandiose goal that you have.
Then, beneath that, break it down into sub-goals or purposes.
Then you define plans to achieve those purposes.
And the plans are broken down into programs, projects, etc.
When you do it this way, then you can step back and see that the little tasks you’re doing are in alignment with the larger plans, and hence your purpose, and your goals. This allows you to get specific for what you’re shooting for (very important), but also know that everything has a direction to it.
Natalie Sisson
A Painted Picture is a clear vision of where you want your business to be, three years from now.
He [Cameron Herold] suggests you get out of your office or normal working domain (which for me is never normal) to actually write it.
It’s a really interesting exercise to go through each section of your business (and your life), writing out your vision in the present tense.
It’s powerful too. It’s as if you’re already there and you can visualise what the future looks like…which is the whole point.
It got me all jazzed up reading about what I wanted my business to become. Even though I’m not there yet, seeing it written down on paper, just gets me excited.
It took me about two hours in total and it was challenging, and also fun. I mean you get to let all your inhibitions go and dream up a grandiose vision for what you really want your business and life to look and feel like.
When we ONLY focus on our vision for our business and our life, then it makes it much easier to do everything in our power to make that vision a reality.
Each of our goals we set, and the strategies and objectives that support them, suddenly become so much more doable, because we have the big picture staring us in the face.
We have the WHY we’re doing what we’re doing. Then we do everything in our power to stay true to it.
Bogdan Condurache I believe that it was Benjamin Mays who said:
“The tragedy of life doesn’t lie in not reaching your goals. The tragedy lies in having no goals to reach.”
This is perfectly true for me and talks about setting any kind of goals for yourself, be it small or high-sky. Of course, setting the goals high-sky will make it very hard to achieve them and will probably discourage you along the way, so I wouldn’t actually recommend that, but from my personal experience the key is to set intermediate goals or step-by-step goals, which are easier to achieve and will motivate you just enough to keep going.
I can actually share a bit of personal experience from my own career path: after graduating college and getting a major in Financial Banking & Insurance, I decided I don’t really like this field of work and wanted to do something in the graphic design business, which was just of a hobby for me at the time. This was something I have never studied seriously, and I didn’t know a whole lot about the industry, but I felt that this is what I really wanted to do and my long-term goal should be to have my own graphic design studio and be successful at it.
So …
I started splitting this long-term goal in smaller pieces
… knowing that this would take a lot of time and effort to get there, but having an achievable goal in front of me would motivate me just enough to keep going.
This got me to my first goal which was learning the trade, that I have achieved mainly by getting an internship job with a graphic design firm and also studying design tutorials and online classes. After a few months, I have learned the basics and “stolen” a few tips & tricks from my colleagues, so it was time to move on, setting a different goal.
Along the 7 or 8 years that had taken me to finally achieve my goal, I have set and achieved a lot of different goals, like: “getting a better paid job,” or “trying to be more creative” and “getting more creative responsibilities” and so on, until the skills, confidence and experience had all build-up enough to start on my own. Also, meeting cool creative people with the same drive as me, has finally helped me bite the bullet and co-found ThemeFuse (and PixelKit later on). Of course, this is a goal that I now consider an intermediate one, as I have moved past and set higher expectations, but still taking them one step at a time.
So, in my opinion setting smaller goals is the right way to achieve a bigger, high-sky goal.
Setting smaller goals is the right way to achieve a bigger, high-sky goal.
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Also, it’s very important that you have passion for what you plan to do, because without it, just setting the right goals will never be enough.
Step #3: Going for a minimal viable product or not?
Nowadays, it seems like we’re witnessing a major product launch every week, or a success story that’s extremely impressive. As a result, we trick ourselves into thinking that whatever we aim to create has to be huge, has to have a ton of features and offer a ton of benefits. But then we lose our confidence when we find out that building something huge also takes huge time and huge resources.
How to overcome this? Should we go for a minimal viable product instead? Is it really that effective? And can we gain confidence by building a very simple solution for just one pain first, and then expand over time?
Demian Farnworth:
Much better to build the audience first. That way you can learn what they need and then give it to them. Most people and businesses have it backwards. They build the product first and then try to find the audience. Of course, there are exceptions. Regardless, do your market research.
Adam Connell The problem with creating a product with a huge number of features is that sometimes we can overcomplicate our offering.
I’ve seen too many start-ups that roll out a product where it seems like even the founders aren’t exactly clear on how the product can be of value.
I’m talking about the kind of sales pages where you look and end up thinking “Yeah, but how is this going to help me?”
Sure, the copy comes into it but when you’re trying to solve too many pains all in one go, you can end up tripping yourself over.
I believe the best way to start off is to:
Step #1
Identify the biggest pain point … Step #2
… Solve it first.
You will be clearer on who the product is for and that will reflect in how you position the brand.
The bonus here is that creating the product will take up fewer resources and you will accomplish it quicker.
You will be able to get feedback quicker and get early adopters on board.
This makes things easier for you in a personal way and also financially.
You can then shape the rest of your product roadmap around the bigger picture that you have envisioned for your product (as well as customer feedback).
When you’re trying to solve too many pains all in one go, you can end up tripping yourself over.
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Ruben Gamez
I like the idea of starting with a smaller goal as a starting point. With Bidsketch, my original goal was to learn how to make money from a product. I went very niche because of this and planned to apply what I learned to the next product. Once I accomplished my initial goal, I realized that I could continue growing the product, so I simply set a new goal. I’ve done this four or five times now.
For me, this approach of smaller quick wins keeps me focused and motivated.
I think too many people aim for huge goals with unrealistic timelines. You obviously should have a goal that motivates you, but keep in mind that your goals (and approach) will change over time.
Mike McDerment
The answer to something like this isn’t binary – it’s about philosophy and approach and context, more than hard and fast rules.
It’s also about psychology – let’s start there.
Whenever you encounter something overwhelming – and there are lots of those things in a start up – you need to take a step back, and focus on what you can control.
… you need to take a step back, and focus on what you can control …
You can’t control what other people are going to do. You can’t control the fact that your competitors are massively outgunned in terms of resources, but there are things you can control – like managing to your next milestone. Stay focused there – however seemingly insignificant that milestone may seem because execution is just about everything when you are a startup.
WRT to philosophy, I think there are a bunch of ways to approach this. Philosophically, I think you want to play to your strengths. So when you are small, chances are any users you have are early adopters – people that found you before anyone and take pride in that. This kind of audience is encouraging and supportive as a rule – it doesn’t take as much to convince them like a mainstream audience.
The consequence: you will be celebrated (and you should celebrate progress), whereas the big guys need you to blow their mind or it’s like, “who cares?” and the difference is entirely about audience maturity and the philosophy and approach you apply to assessing your progress as a result.
Step #4: Get only the essential education that you need
Every online business owner tries to learn and acquire new skills every day. But at the same time, we often lose our confidence when we realize how much there is to master and how seemingly insignificant we feel.
Do we need to be spending hours every day acquiring knowledge in order to become confident? Or is it actually a trap because we will never feel competent enough? How to tackle this and how to seek the truly essential education we need?
Danny Iny
Cliff Ravenscraft
I think that acquiring knowledge is important and helps us bring additional value to those who follow us. However, I don’t see a direct correlation to how much knowledge you have to the amount of confidence that you have.
Many people suffer from what we like to call “Imposter Syndrome.” The fear that we are not competent enough come from the fear that others know more than we do and that we will be judged for where we are in the journey of our area of expertise.
I believe that everyone can confidently step out into this world, no matter where they are in the journey, and avoid the “Imposter Syndrome” by simply focusing all communication in these four areas.
Start with what you have experienced so far in this area of expertise. Tell people “your story.”
In many cases, the more mistakes you’ve made, and and you share with your community, the more relatable and likable you will seem to those who are fellow strugglers on the journey.
Of course, you should also share your successful experiences as well. Don’t worry about those who will be offended by your sharing, telling you that you sound boastful. The fact is that sharing your success stories, and giving the details on how you succeeded, will do much to encourage and inspire others.
Share the challenges that you are facing now. Don’t pretend that now that you have a platform in this niche that you no longer face challenges. By sharing them, again, you are being more relatable to those who follow you. Also, there is a great chance that many, who are further along in the journey, may reach out to help you overcome those challenges.
Share what you are learning right now and how you plan to implement what you are learning.
Obviously, this means that you are actively learning new things. I make it a point to read books that are devoted to my personal and professional development. I listen to podcasts from experts in business, social media, technology, etc. I’m always learning something new. Being a great student of life makes you a great teacher for your community.
Share what you hope to accomplish moving forward. DREAM BIG DREAMS. Know where you want to go. Have a destination in mind. This is the only way that you will get there.
Also, if you don’t know direction that you are heading, why should anyone follow you?
By focusing on sharing those four areas of your life, you can lead with great confidence! If you are always true and honest about those things, you can not be considered an imposter. Just be yourself and know, for sure, that many will criticise you for that.
You don’t need to spend hours a day, every day, gaining more knowledge to become competent and confident enough to deliver a message. You just need to grow some thicker skin and then put that skin in the game.
Yaro Starak
In my life as an entrepreneur true confidence has only come from achievement.
Tangible outcomes are what drive motivation. Of course learning is necessary – and some of the best education comes from the projects that don’t succeed – so you have to find a balance.
The best advice I can offer is:
Always acquire knowledge that is directly correlated to an outcome you are working towards today.
Only study what you need to know to solve today’s problems, and put into action what you learn immediately.
If you are unsure of what path to take, then the problem you have is a decision making one. You must study what you need to know in order to make the decision of what path to take.
Step #5: Master the craft of planning
Lack of confidence leads to procrastination, and that sometimes leads to complete inaction. Unfortunately, the enormity of the project at hand – building a business – literally paralyzes many entrepreneurs.
How to master the craft of planning? How to create a good plan that breaks down a large project into doable chunks? Are there any quick hacks we can implement to feel confident about executing our plan one step at a time?
Adam Connell I’m a firm believer that anyone can accomplish anything that they put their mind to, whether you lack self-confidence or not.
The key is passion; we have to believe in the product we create.
When planning out your project you need to break it up into smaller tasks and create a complete road map for your project. They need to be manageable otherwise they may start to become tedious.
It’s important that the plan is as thorough as possible, consider everything from creation to marketing and growth while considering the possibility that you may need to react quick to demand in future if your product takes off.
Consider a time frame but keep things realistic and allow yourself some room to manoeuvre.
Try not to let falling behind schedule phase you, you cannot account for everything and sometimes things don’t go to plan.
But, if you can consider potential road blocks before they happen and account for them you will make things a lot easier for yourself.
Prioritize your tasks but be prepared to re-evaluate these as your project progresses.
Most importantly, try to make things as easy as possible, consider what tools are available to make managing the project as easy as possible and think about how you can make your business as process driven as possible. You will love how much more efficient processes can make your business, you need them in place early on.
… try to make things as easy as possible …
Ruben Gamez
I like to keep things simple, so my plans aren’t very detailed. I usually start with a goal and then work backwards from there. From a high level, what do I need to accomplish this goal? I end up with a rough idea of what needs to get done, then spend some time prioritizing.
At that point, I add about two weeks worth of tasks to my active list and only research as the need comes up – not weeks before the project has started, but right as I’m working on those specific things. The only exception might be with risky tasks. For online businesses the biggest risk is building something that people don’t want to pay for. So it’s probably a good idea to make your first task testing your assumption that people want to pay for whatever you’ll be providing.
Anyway, going back to planning, the idea is to move as quickly as possible and stay focused. I do this by creating a high level plan, prioritizing things that matter while delaying ones that don’t (like a business account), testing assumptions, and breaking down my work into four hour tasks (maximum one day tasks).
Bamidele Onibalusi
I would first advise not to become too obsessed with planning, as that alone can deter you from your main goal of getting things done.
I believe the most effective way to go about this is by breaking down each task into the smallest possible task that will take the smallest amount of time necessary. Once this has been done, you should start working on the most rewarding tasks, that will deliver the quickest results.
Seeing these results will motivate you and give you confidence to proceed with your other tasks.
Bonus round!
Defeating confidence problems
What were the main confidence problems you experienced in your career and how did you overcome them?
John Lee Dumas
David Risley Not having promotions work as well as I had hoped. Hey, it happens. The best way to overcome it is to have something pulling you forward so you don’t stop. For me, its my family.
Jaime Tardy I wasn’t confident in my value at first – and I had a hard time asking for what I wanted. Like when I found my mentor, it took all of my strength to send the first email to him!
Demian Farnworth Thinking I could compete with the big boys and girls. You cure that insecurity with hard work, training, education, and experience. Everyone starts at the bottom.
Bogdan Condurache During my career as a graphic designer, I have encountered many times what I would call “feedback fright”. What I mean by this is getting a bit uneasy about showing the client a pitch or a design proposal that I have have been working on. Lack of confidence made me doubt my initial feeling of “wow, this is great stuff” and made me start questioning the whole design style, idea, execution, etc. “What if the client will not like this?” or “What if the idea is too bold or not bold enough?” are questions that fuel the “feedback fright” syndrome and can influence your work in a bad way, because what happens is you start changing the proposal without a real reason, making it worse actually.
I have somewhat overcome this (I still experience it from time to time) by making sure the foundation of my work is sound and that I personally like the outcome – because if you don’t like it yourself, there’s a big chance no-one else will like it either. Also, getting better at your job and accumulating experience will increase your confidence, so even if someone doesn’t like your work and gives a bad feedback, you can fight back with good arguments and ideas that come from experience and gut feeling, challenging the client’s feedback. I know this is very specific stuff, from a specific industry, but maybe you can extrapolate it to a more general business model.
Cliff Ravenscraft My greatest confidence issue that I’ve faced in my business was pricing. Especially when I’m offering a new product or service that I’ve never offered before. Questions like, am I good enough, will believe believe I’m worth this price, etc?
I overcame these fears by putting my new products out there with a price that was just beyond my comfort zone and allowing my clients to tell me that I should be charging much more than I charged them. In every product or service I’ve ever offered, I’ve ended up more than doubling the price of what I originally charged. It was putting myself out there and not failing that gave me the confidence to grow in this area.
Yaro Starak My main confidence issues originally stemmed from being so different to everyone else around me. All my peers went on from school to university to jobs. I had no desire to get a job, and I knew I wanted to be my own boss, but without any local role models it was difficult to believe I could pay my bills with my own business one day.
I have to admit during the first few years out of university I was very lost and had little confidence. However as I started to get results and slowly generated enough money to live independently I realised what I was doing was so much better than anyone else around me. Eventually I became proud of being an entrepreneur, and people came to me asking how I did it.
I learned an important concept I call the “success ladder,” which is one tool that can give you confidence, step-by-step, as you strive towards full independence as an entrepreneur.
The success ladder is a simple idea – you celebrate each step forward and use it as the building block for the next step. When you apply this principle every day, you see how the small tasks you complete lead to bigger results. It becomes stronger and stronger as more results come your way, until you reach a point where you feel as if your results are inevitable – a very powerful form of inner confidence.
Danny Iny
Getting instant confidence
What would be the one thing to do right now to gain some instant confidence in your business?
Demian Farnworth
Jaime Tardy One thing I LOVED to do, was to have all of the kudos, testimonials, etc in one place. When I wasn’t feeling confident I would go back and read those. They were amazing people singing my praises, and while I was hard on myself – it was easy to see how much value those people got out of working together.
Bogdan Condurache The one thing i did was to make sure we built a product that people need and want. If you have something that people want, in our case great looking and perfectly working websites, you build a client base that appreciates your work and buys your stuff. And with this appreciation comes confidence, you start feeling more secure, more sure of your decisions and ultimately more successful. As i said earlier, having great foundations, like passion and skills for what you do, is the key to being confident and having a successful business.
Yaro Starak Do something. I learned a long time ago that you must focus on output – on creation, not just consumption. Consuming things, whether education, or entertainment, will not lead to an outcome. Only creating things for the consumption of other people leads to the results you want, so get out there and create something for other people.
David Risley Generate your first dollar. From there, it gets easier.
Mike McDerment This is a tough one – it really is a question that varies company by company, person by person, day by day. The answers for me have evolved over the years because the measures of progress have. To begin, it was customer validation in the form of feedback. Then it evolved into watching product usage, and eventually in time it was revenue added. But normally what gives me confidence are subjective things. For example, I get fired up when we hire someone awesome and see them getting ramped up on our business. That gives me confidence, because I know a super capable performer is going to be applying themselves to making FreshBooks a great company for other FreshBookers and our customers.
Being a successful entrepreneur
Is it possible to be a successful entrepreneur without being confident?
John Lee Dumas
Mike McDerment One of the best things I ever read – sadly I can’t remember where – is that every “successful” person has had moments where they have doubted themselves and felt like a failure at the very moment the world is exalting their “success.” I know I’ve had moments where everyone around me thinks “this is a big success” and is patting me on the back, but for me it’s not like that – all I can see is the work ahead and it’s daunting.
So I guess what I take from this is, successful or not, we are all human – we have moments of doubt and fear. I think there is a tendency to believe this is not true of “successful” people. What I’d say to those who aren’t feeling confident is, that those internal demons are a source of motivation. Control them. Channel them. But don’t for a second think you are the only one. You are not the only explorer of the terrain you are on, and as lonely as the path of building a company can be, you have to keep that in mind and just focus on what delivering on the things under your control.
Adam Connell I believe it is.
In some cases I’ve known people to turn their lack of confidence into a positive attribute and go on to do great things purely by striving to do better.
And for others, the confidence comes along when achieving success.
Wow, that was a lot of information to take in all at once! I’ll let you process this in peace, but remember to take action on what you’ve learned here as soon as possible.
Also, are there any confidence issues you’re experiencing right now? What one thing are you planning to do ASAP to solve this issue?
In the meantime, don’t forget to share this with whoever might consider the information inspiring.
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13 Successful Entrepreneurs Share How to Gain Confidence When Starting an Online Business | NewInternetOrder.com
Earlier this year, I’ve written a few 
While writing last week’s post about 
Last year, Michiel has written a few posts about social media marketing and how you (and we) could improve on it. This gave me the idea to highlight one of the marketing techniques that’s working out pretty well for us: email marketing.
