Mat Casner Freelance CEO
Freelance CEO podcast
The Freelance CEO Podcast with Mat Casner
Ep. 10. How to Make Risky Decisions as a Freelancer With Confidence
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Have you ever laid awake at night with a difficult decision to make, do risky decisions, make you afraid to move forward? Listen, being a freelancer is a risky business and it’s full of decisions that involve risk, but you don’t have to live in fear. It is possible to know how to make risky decisions with confidence so that you can step into new and exciting realities.

So how do you know if you should stop or you should go, you making risky decisions is kind of a part of life. But when we, we think about our freelance businesses, seems like a lot of times we are gun shy. It seems like we’re afraid to move forward. We’re afraid to take possible action because of unintended bad consequences.

We get paralyzed by fear and we get stuck in neutral and we are afraid to move forward. And I get that. It’s totally understandable. And fear is not a bad thing. And I’m going to talk about that here in a little bit, because fear is actually a, a very important defense mechanism that’s built into us. However, sometimes I feel like as individuals, even myself included, if I allow myself to be, you know, muscle around by fear, then perhaps what might be a good opportunity I might, you know, I might hesitate on because I haven’t really properly assessed the risk and how that potential risk could be a potential benefit for me. I can tell you that over the years that there have been lots of risks that I have not taken.

And I think for the, a lot of the right reasons, however, I can also say that there were a lot of risks I didn’t take. And it was simply because I didn’t want to, to lose. I didn’t want to fail. And those decisions actually probably cost me more than, than, than not taking the risk itself. So there are lots of lessons to learn, and this is no way a black and white sort of a thing. But I feel like if we, the skills to make educated decisions, when there is risk involved, then we can in essence move forward and, and move into these new and exciting areas that will potentially open up new opportunities for us, if we’re not afraid to move forward, even with a little risk.

So what I want to do is I want to share with you three things that I’ve done in my own life over the past 20 years, when I am faced with a risky decision, what do I do and how do I move forward with that decision?

So step number one is always assess the risk.

I mentioned before that fear is a natural and healthy defense mechanism.

It’s there to protect us from danger. We should listen to it and heat it, but listen to me here. We don’t have to be intimidated by it.

I think there are two types of risk. There is good risk and there’s bad risk.

Bad risk to me is almost always harmful and there’s very rarely an upside.

I might even call bad risk a lot like foolishness.

I really can’t think of a good example where anyone would have a consistent, positive outcome by taking a bad risk.

They, they end up badly most of the time.

So being able to identify a bad risk is a really good thing. Now on the other side, a good risk

Is a risk that carries potentially good rewards.

But it’s not without risk.

Here’s a great example. Getting my driver’s license as a teenager is an example of a good risk that I took.

Getting into a car, and this is the same for anyone.

Getting into a car, carries with it, a very real and present set of risks, not just to ourselves, but to those that are on the street with us. Every time I get in the car, I do my best to manage the risk as best I can to keep myself and the others on the road as safe as possible.

And I have to trust that the others are doing the same.

So there’s risks there, but here’s the thing. The real benefit of being able to drive a car is that I’m able to travel easily and I can do things that would not be possible without motorized transportation. So there’s a big upside to being able to drive a car, good risk, right. Throughout our life. We are constantly assessing risk and we’re making choices based on their assessments.

So number one, assess the risk, know what risk you’re looking at and if it’s good or if it’s bad.

So step number two, don’t be afraid of failing.

Sometimes I see this in my own life as being the criteria that kept me from taking a risk.

I was afraid to fail. I’m a perfectionist at heart, and I kind of liked to make sure that every duck is in a row and I want to do something really, really well. But here’s the deal guys. Every time we do something new, we’re doing it for the first time. And I can tell you that I rarely do something on the first time with excellence.

Usually I’m trying something new and I’m learning from it.

The faster you can get past that first time, the sooner that you can learn, grow, and improve mistakes are just a part of learning.

The brightest minds on our planet didn’t reach their greatest achievements. The first round out of the gate.

It took time sometimes years or decades of trying and learning before they reached their pinnacle achievement.

We’re the same way, guys. We shouldn’t let the fear of failure. Stop us from doing something new.

We can’t let mistakes hold us back. When you fail, you either win or you learn.

There’s really no downside.

So don’t let the fear of failing. Keep you from trying something that might seem risky.

With there’s an opportunity to fail. Take it as an opportunity to learn.

Now step number three.

This is the process that I follow when making risky decision decisions with confidence in my own life.

Here’s how I do it.

Step number one, I determine the worst case scenario for this decision. So I look at the risk. I look at the opportunity and I ask myself, if this thing goes entirely south, how far south does it go? What are the real implications? What are the real consequences? What’s the reality.

What really happens?

Now again, that’s healthy. I think if we look at a situation and we can determine that if I make this decision, here’s the worst possible thing that could happen.

When I get in my car, what’s the worst possible thing that could happen? Well, I could get in a crash and I could die.

I could get in a crash and I could kill someone else. Those are real risks. Those are real outcomes that could happen. It could happen to any one of us, but I don’t let that decision stop me from getting in my car and going places.

There’s a bit of that risk that I’m assuming. All right, that could happen.

If something happens, I’m in a wreck. Well, I’m probably going to go to the hospital or I’ll have to call the police, or I’ll have to call my insurance agent or whatever the case might be.

There there’s a real, there’s a real, a reality that could happen by taking a risk. Our, our, our lives are no different.

When it comes to freelancing. When you take a job with a client, you’re putting yourself out there, you’re serving that client and hoping that you can do the best job possible.

You hope for the best outcome, but maybe it doesn’t turn out well.

Maybe, maybe the job doesn’t go. Well, I’ve had plenty of those in my life.

What are you going to do? Well, you’re going to learn from the experience. You’re going to take what you’ve learned, the things that didn’t work in that experience, you’re going to correct them. You’re going to make them better. You’re going to figure out what it is that you did wrong. And you’re going to make sure that you don’t do that again.

So that the next time you have a chance to serve a client, you don’t make that mistake.

So there’s nothing there’s nothing wrong with, with, you know, taking a risk, as long as you know, what the worst case scenario might be. Now, step number two, after you determine what the worst case scenario would be, you need to plan a course of action. That would be your response in case of the worst case scenario. A

So let me just, just an example here. When I went freelance full-time was 15 years ago and I had the opportunity and I had a decision to make, did I step away from my salary job that was paying me consistently week after week, month after month in exchange for a job where I was basically in the driver’s seat.

And, and back in those days, I didn’t have any guaranteed. I had no assurance that freelancing was going to be something that I could do full time. I just had an idea and I knew that there was a chance that I could make it work.

So in my mind, I had to make a decision. Is this something that I move forward with or not? So in my mind, I determined that the worst case scenario is that after three months, which is how much money I had in the bank to sustain me and my family, I would take an ad valuate my situation after a three month period.

And before I bled the bank account dry and make a decision. If I thought this would continue to work, or if I was going to have to go find the other job, the worst case scenario was I wasn’t able to continue to bring the income in.

The plan of action that I came up with was I go out and find another job.

I go work for somebody else again.

I’ve done that before. I know how to do it. I could do it again. If I had to. All right, that’s the course of action that I had for making the decision to become a full-time freelancer.

So for whatever risk that you’re assessing, take a look at the worst case scenario and plan, of course of action. What are you going to do if it comes to it?

We never hope for a worst case scenario, but if you plan for it, you have a recourse.

You have something that, you know, you can do if you get into that situation.

So step number three is you look at your course of action and you determine in yourself if you can live with yourself and be at peace with that plan of action.

I had to look at my course of action in becoming a full-time freelancer. And I said to myself, listen, if I don’t make it as a full-time freelancer, I will go back and I will find a new job. And I had to in my own mind and heart, be at peace with that decision.

To know in my mind that if things didn’t go well and things didn’t work out, like I’d hope they would, that I could go back out and find another job. Doesn’t mean I would quit freelancing. It would just meant that I was going to have to go back and find another income. So when I got to the point in my own mind that I felt comfortable with that decision, then I felt free to move forward and become a full-time freelancer.

I had enough things figured out there were a few things that I didn’t know, but I knew if things didn’t work out, like I planned, I had recourse. I had a plan of action that I could enact and I could get back on track.

So once I made that decision, I was able to move forward and start freelancing with confidence, knowing that if things didn’t work out, I had a fallback. I had a plan.

So that helped me and has always helped me when making a risky decision to follow those, that process.

Number one, assess the risk. Find out if it’s a good or bad risk. Number two, don’t be afraid to fail because when you fail, you either win or you learn. And number three, follow the process for making the decision by number one, determining the worst case scenario, determine how bad it could ultimately be.

Number two, plan, a course of action, just in case the, the, the worst case scenario happens. I contingency plan. And then number three, see if you feel at peace with your contingency plan, if you’ve have a piece that you can enact in the contingency plan and be okay, then you have a green light to move forward.

Hey, I hope this was helpful for you. Like I said, it’s not black and white. We have to make our own decisions and everything basically ends up resting on our own shoulders.

But I feel like if we have a process and can be wise with the decisions that we make, we can make decisions that will help us move forward and take advantage of opportunities that are in front of us.

God bless.