Starting a business or side hustle is no simple task, and don’t let anyone tell you differently. There are lots of moving parts and plenty more factors to consider before you really get things off the ground. But if there’s anything that holds people back unnecessarily more than anything else it’s this: fear and self-doubt.

Nothing strikes at the heart of entrepreneurship quite like it. So if we’re going to be successful, we need to be proactive and smash it before it smashes our efforts.

Fear can be an enemy or a motivator.

To be clear, fear isn’t necessarily all bad. Fear can make us more cautious and cause us to proceed more carefully than we otherwise might have, potentially protecting us from pitfalls and problems that other people waltz right in to.

But it can also be paralyzing, causing us to seize up and not put one foot in front of the other – potentially costing us precious time and resources.

Thoughts like, “but what if I fail?” or “I don’t think I’m good enough for that” or “there are people who are better at it than I am” can hold you back when you ought to be excelling.

Lest I be misunderstood, I’m not talking about some new age self-help garbage here. I’m talking about having a realistic mindset that understands the risks and rewards of business, being aware of the potential pitfalls and pushing forward confidently knowing what to do.

Helpful fear can keep you from making some of the same mistakes that others have. It can keep you from being reckless or unwise.

It’s true that many businesses don’t succeed. That’s indisputable. But knowing that fact – and not wanting your own business to fail – you can learn to avoid the mistakes that others have made. In that regard, some measure of fear and doubt can be healthy. But only if it’s a tool that helps to propel you to do what you need to do and keep working hard in a healthy way.

Fear that paralyzes you and makes you afraid to take action is the fear that needs to be overcome.

Learn all you can.

Whether you’ve already started your side hustle or you’re about to, take some time to learn how to do things best. No matter what you’re doing, there’s most likely someone who has tips and tricks you haven’t thought about.

Learn what it takes to be successful in your chosen side hustle and find out what you need to study in more depth.

Let’s say you want to start a new photography business. Take some time to learn about photography as a business. What kind of equipment will you need? How much time will it take to start getting clients? What kind of marketing should you look into and how much will that cost? Are there ways to grow your photography business without too much time and money?

The more you can learn up front, the fewer surprises you’ll have along the way. And the fewer surprises you have, the less likely you’ll be to be discouraged.

For example, if you know up front that you’ll have to spend a thousand or more on a good camera, that won’t come as a shock and major setback when you get to that point. Or if you know you know that it will take time to build up a reasonable portfolio that will enable you to bring in clients, you’ll be mentally prepared and the task won’t seem as daunting.

Remember your strengths.

Some of us do certain things better than others. That’s not something to be prideful of, of course, and we should let our strengths make us prideful people.

But there is a point at which it’s healthy to recognize, “I’m good at ____.” For example, one of my strengths is writing. I love to write, and I’d do it all day every day if I could. (Don’t tell my middle school English teacher, now.)

When I get discouraged, it helps me to remember that I do have strengths that can help me succeed.

We should never let our strengths make us proud or arrogant, of course. We know that we’re not good at some things also, and we need to maintain a realistic view of ourselves. But neither do we want to get so down that we forget that we do have skills that allow us to create value.

Ask for help when you need it.

There is absolutely nothing wrong with needing help. But there’s a lot wrong with needing help and not asking for it. Do you understand the difference? As you build your business and brand, there will be things that you’re going to need help with.

As the saying goes, teamwork makes the dream work. There’s no better way to grow your business than networking with other likeminded people. I don’t care what kind of business or side hustle you’re running or thinking about starting. You need to connect with other people who have similar goals.

Get advice from people you trust and learn what’s worked well for others.

Reach out to people in your niche or who are trying to accomplish the same goals and get some advice. I’m a member of a couple such communities, and I’ve found them very very helpful and encouraging to me when I’ve needed an answer or some input. I would encourage you to seek out the same thing for yourself and don’t neglect the importance of working alongside others.

Take time for yourself and family.

Working all the time and not taking time off is unhealthy at best and harmful at worst. Don’t underestimate the important of your mental health, and it’s hard to care for that when you throw yourself into work all the time.

You might be thinking, “What does this have to do with overcoming fear and doubt in my business?”


Taking time for yourself and taking time to spend with your family is essential for a healthy work / life balance. You can’t be at your best if your life knows nothing but work, and that grates on your overall mental wellbeing over time.

I’ve been there.

Remember what’s most important at the end of the day. And it’s not your side hustle. Not ultimately.

Working hard is admirable, and you should expect to work hard if you want to be successful. But don’t let that be an excuse to neglect the people in your life who care about you or to not take time for yourself and spend time not working occasionally.

Rest is a good thing if done well. In fact, I would argue that it’s impossible to work well without resting well.

Set realistic goals.

One of the worst things you can do for your business is to have unrealistic expectations and goals. Whether you’re starting from zero or have been working your side hustle for a while, think about some goals you can realistically expect to achieve.

For example, if you’re wanting to make money writing on Medium but you’re not earning anything yet, it’s not realistic to expect that you’re going to hit $500 your first month in the Medium Partner Program. Could it happen? Sure. Is it likely? No.

But if you start off saying, “I’m going to try to make $25 this month” and you make $35, you’ll have beaten your goal by $10. On the other hand, if your goal was $500, you’d be $465 short and probably find yourself a bit discouraged.

The next month, you could try for $50 and then $100 and then $200… gradually up and up toward $500 and beyond.

Or, if you’re trying to get traffic to your blog, try for 50 views one month, 100 the next, 200 the next, and so on. Don’t start out thinking you’re going to reach 10,000 views the same week you launch your blog. You’ll be sadly disappointed and discouraged if you aim for the stars from the starting gate.

On the other hand setting and achieving attainable goals helps to keep you motivated. If you constantly set goals that you never achieve, you’re likely to get discouraged. You’ll start to doubt that you can actually be successful.

After a while, that kind of thing grates on a person.

When you set and reach goals that are achievable, you show yourself that you can do this and are encouraged. It might seem silly, but this is something that helps me.

Celebrate the little wins.

As you hit more and more goals that you’ve set or get a sale or get more followers or meet whatever metrics you’re hoping to hit, celebrate. No, you might not be where you want to be yet. You might have 105 followers on Medium when you’d like to have 1,005, but take time to celebrate the win of getting to 100 followers and beyond!

As you grow your audience, celebrate your chosen milestones. As your blog grows in popularity and starts pulling in more traffic, celebrate the win.

Don’t get so hung up on the fact that you’re not where you want to be, and instead focus on the fact that you’re better off than where you were.

Having 105 Medium followers is better than having 25 followers. And if you have 105, you had 25 at some point. Celebrate that growth.

This goes with the previous point – setting realistic goals. This is a great way to keep yourself motivated for the long run.

Recognize that there will be setbacks.

This is a big one. Lots of people start out in a side hustle with unrealistic expectations and fail to recognize the fact that there will be setbacks. I guarantee it. No matter what you do, there will be setbacks and discouraging days.

It’s just a fact of life and business that there will be days that are discouraging. Preparing yourself for that reality early on will help to keep you motivated when those days come. Setbacks can take lots of forms and come in varying degrees.

If you’re blogging, you may find that you don’t get the traffic you were hoping for. Your Medium articles might not earn what you were hoping or your views might fluctuate more than you expected. You might not get the product sales you were wanting.

It happens. The answer to those setbacks is not to throw in the towel. Instead, mentally prepare yourself now so that when they come, you’ll know to keep on pushing forward and working diligently.

Mindset is very important for your business.

I strongly believe that our thought lives can have a profound impact on our businesses – and whether or not they succeed. That’s true simply because our thoughts impact what we do and whether or not we put in the effort and time required to make a difference for our side hustles.

If I get so down and discouraged that I don’t think I can even work on my side hustle, then will I? Not likely. On the other hand, if I approach my business with confidence and a willingness to work hard even when I encounter setbacks and have bad days, how much better do you think I’ll fare?

This is what I hope to get across to you, dear reader. It’s very very important to pay close attention to your thoughts. Not because you can “manifest” this or that. Nah. None of that new age garbage. But it’s important to pay attention to your thoughts because your thoughts became habits and behaviors, and those habits and behaviors can make or break your business.

So make the choice to develop a healthy mindset. I would venture to say that everyone going into business of any sort has some measure of fear and self-doubt here and there. But what you do with it can make all the difference.

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