You can’t guarantee anything — except that you’re going to be uncomfortable at different points. Here’s how to make the best of it.

When you decide to become an entrepreneur, you’re choosing to walk the road of the unknown. That’s what you’re getting into. There’s no other way around it.

You could run out of money. You could get featured on the front page of the Forbes, then have to scramble to handle the influx of new business. You’re going to be in uncomfortable, weird, bad and great situations because your job is dynamic. Every month that you grow and your business changes, it’s going to be different.

You can’t guarantee anything — except that you’re going to be uncomfortable at different points. And, when you know that, you can decide to start practicing getting out of your comfort zone.

Here are a few ways to do it.

Do something that’s uncomfortable on a regular basis

Sit down and make a list of all the things that make you uncomfortable. If eating new foods was near the top of the list, make it a priority to try a new food on a weekly basis.

Nine times out of ten, you won’t like the new thing you’ve tried. But that one time out of ten will be amazing. You can do something similar, but it doesn’t have to be with food. Maybe it’s just taking a different route to the office or trying a new morning routine — anything that will get you comfortable with newness and discomfort.

Start really small.

And don’t think that when I talk about trying new things, I mean making huge, sweeping changes. It’s better to start really, really small.

I have social enxiety. I’m terrified of heights. But I’m not going to overcome these fears by going on a Skydiving Adventure in a plane full of willing people to jump out and do their trick in the air.

Instead, to get rid of my fear of heights, I might go on a Gold Reef City Rollercoaster ride (anaconda). Or fly somewhere on a plane. Maybe I can go to the Table Mountain and gaze down its steep cliffs for 30 seconds. True, I might not get over the fear itself. But my ability to handle that fear — and any other fear of the unknown, in general — will grow.

Put yourself into different roles.

This quarter, I’m serving in the role of sales and business development (SBD) for Orange Memo. I’m attending networking events, in charge of generating new business for the company, pitching the business to potential new partners, managing client relations, and being the key contact for partnerships to customers. I’m not an expert in any of these things, so I’m out of my comfort zone. I do a lot of these things in different capacities — just not in my area, which makes me uncomfortable.

We are currently recruiting Sales and Business Development Managers but going through the process myself helps me understand what it is I’m trying to solve with this role. Without this discomfort-inducing exercise, I wouldn’t really understand what the role is, what the metrics are and what it’ll take for someone to be successful. But if I do the work — even for a few hours a week or a few hours a day — I’ll know more about it.

Push yourself, with exercise.

I lost my fear of public speaking a few months ago, when I proposed to facilitate a duo workshop (CV Success Masterclass and Business Startup Workshop) to 50 interns who were not sure how to navigate their career. I figured, if I can survive that, there’s not much else I need to be scared of.

You don’t have to be into high-adrenaline sports to get this benefit. Any big exercise, or activity-related, goal will work. Back in 2020, I’d never talk to a room of 50 delegates. But I set a goal for myself to test myself and facilitate a duo workshop. I enrolled on a presenting online course, researched, put together the content and I facilitated the CV Success Masterclass on a Thursday and Business Startup Workshop on the following day, Friday.

The process was overwhelming, and the actual experience definitely uncomfortable. But when I got through it, I couldn’t help but think, “If I can do that, why am I so afraid of business decisions?” By pushing myself mentally, work ethics and testing my limits, I was able to apply the same thinking that made what I learned preparing and facilitating the workshops applicable to all aspects of my business.

Remember the things that make you comfortable.

I have social anxiety. I’m lucky enough to have a small loving family to go home to. That’s my norm. So, even when I’m uncomfortable during a social event, I know that, at night, I’m going to go home and be in comfort.

You don’t have to have a loving family to be successful as an entrepreneur. But you should find what’s true for you. Find the things in your life that bring you comfort, and make it a point to remember them. Knowing you have something comfortable to go back to makes discomfort in business much easier to bear.

How do you get out of your comfort zone, and how do you feel that doing so has helped you as an entrepreneur? Leave me your notes below:

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