Project Management

5 Steps to Overcoming Obstacles in Your Small Business

Published by in Project Management

“The thing that’s depressing about tennis is, no matter how good I get, I’ll never be as good as a wall.” – Mitch Hedberg

Personally and professionally, we’re constantly facing down walls and hurdles. Walls are unlike hurdles, though, in a bunch of important ways.

A hurdle is something that comes up at regular intervals, is easy to see past, and can be overcome with a little effort and planning. On the other hand, you never know when a wall is going to show up, they’re hard to see past, and not many folks can just leap over them.

Walls seem to stand in our way for weeks or months, or even years. They’re the things we see in the distance that take the wind out of our sails (metaphor mixing at its finest).

For example:

  • Your business can never compete with Amazon, so why even bother with X, Y, or Z?
  • Your BMI is 37 and you can barely walk a mile, much less run one, so how can you ever get healthy?
  • You’ll never speak French as well as a native Parisian, so why even bother?

These aren’t hurdles. You don’t overcome them in a single weekend, and their mere existence makes it harder to address the underlying issue. Why work to be better if you can’t be “the best,” whatever that means. It’s standing at the bottom of the mountain with no rope.

Man, I love metaphors.


Overcoming obstacles and loss aversion

There’s a bit of “letting the perfect be the enemy of the good” here. When you’re looking at something as overwhelming as the power of Amazon, it’s hard to even formulate a plan of attack. That’s classic loss aversion.

We don’t see the opportunity in things because we’re hardwired to see the potential losses. Carl Richards summed this all up in a New York Times article on the psychology of investing a few years back:

“We hesitate to change from the current situation because it means having an opinion and making a decision. And with a decision comes the very real possibility that we’ll make the wrong one. Sticking with the status quo feels much better even if we know it’s costing us money.”

Today, we’re going to look at ways to change your mindset, develop a realistic plan, and keep your eyes on the prize to overcome the fear of loss and your walls, all in five simple steps.

Step 1: Set realistic expectations

The first and most important step to overcoming loss aversion is to have a realistic expectation about how things could turn out. If you walk into a casino certain that you’ll walk out either destitute or a millionaire, you’re in for a bad time. Instead, think about what could actually happen and what kind of control you have over the situation.

Take a scenario where you’re opening a store. Let’s say you want to sell camera equipment.

After some success, everything levels out and you start to think about next steps. In doing so, you realize that your biggest competitor isn’t the place across town, it’s Amazon. How in the world are you supposed to compete with Amazon, a $450 billion business?

It’s already happened. You’re in the grips of loss aversion paralysis.

To overcome the problem, rephrase the idea of success in realistic terms. Will you sell more camera gear than Amazon? No. But you could sell more to the local college, by working with the art department. Or you could focus on niche high-end used cameras. In short, you can focus on being a local winner, if not an Amazon destroyer.

There’s no end to the number of very successful things you could do with your business that don’t rely on “beating” Amazon. If you want to overcome your wall, you have to set a realistic expectation about success. Importantly, you have be happy with success you’re aiming at, even if it means Amazon stays in business.

If you set yourself up to be unhappy, even in success, none of the rest of this is going to be meaningful.

Step 2: Develop a plan with an endpoint

The next contributor to what is a seemingly insurmountable wall is that many of the plans we make are unfinishable.

If the plan is “sell more camera bags,” well, that’s not really a plan. That’s just a thing you want to do that has no endgame.

The Lowepro camera bag I ordered yesterday

A real, achievable plan looks more like:

Goal: Sell 350 camera bags this year


  1. Meet with the art department and getting specs
  2. Price out a university discount
  3. Advertise on campus
  4. Run three free workshops during the fall semester

That’s a thing you can do and then be done with. It has a point at which it’s been achieved, freeing you up to reflect, iterate, and set a new plan.

For your wall, the plan is going to be much more detailed and may extend over a longer period of time. However complex it is, each step must play toward the end goal. Don’t generate a whole laundry list of tangents as part of your core plan.

Next, to make sure you’re staying on task, break each item down.

Step 3: Atomize your plan

“Atom” is derived from an ancient Greek word, “atomos,” which means indivisible. An atom is the smallest part of a thing or idea—not counting all the other super small stuff that actually makes up the guts of the universe.

To overcome the wall in front of you, it’s crucial that you break the plan into the smallest possible pieces. The goal of running a marathon is a very difficult goal to fathom. Even at a plan level (run five miles this week, run six next week, etc.) it can seem daunting.

“Run five miles this week during my afternoon breaks” can be broken into:

  1. Run one mile on Monday at 4 p.m.
  2. Run one mile on Tuesday at 3 p.m.
  3. Run one and a half miles on Thursday at 3 p.m.
  4. Run one and a half miles on Friday at 1 p.m.

You would break it up like this because the whole purpose of the plan is to make the wall seem like something that can be overcome. Each step in the plan is a tiny part of the climb. The smaller the steps are, the less overwhelming they are and, thus, the easier it is to tackle each one.

Step 4: Focus on one part at a time

Our whole plan for this plan (our metaplan, if you will) is to make something that initially seems difficult or overwhelming feel as easy as opening a door or waking up before noon. Multitasking is a wonderful human ability, but it’s also the quickest path to burying yourself in small tasks.

Instead of taking on five of your little plan steps at once, focus on getting one done at a time. There will, of course, be times where more than one thing is happening. Maybe you’re negotiating a lower price on a pallet of camera bags at the same time that you’re drawing up some advertising, but these situations should be the exception.

A laser focus can make the long road seem like a series of short trips.

A Kanban board

This is one of the components of the Getting Things Done (GTD) task management system or agile project management. Each task you have is prioritized and broken down into smaller tasks, making each of them a short, achievable subgoal.

Step 5: Accept the results and iterate

Apart from setting the goal, accepting the end result is maybe the hardest part of this whole thing. It’s hard because, in setting a realistic goal, you naturally trimmed out some of your loftier aspirations.

The year is done, and you’ve made yourself the biggest camera dealership in the city by working closely with the university and increasing your targeted sales. You’re still not as big as Amazon, and you may still be smaller than the place in the neighboring town.

That can sting—but only if you let it.

Instead of focusing on what you didn’t do, though, focus on what you’ve accomplished. You have to do it that way because it’s the only way to keep up the momentum you’ll need to start the whole process over.

By the time you overcome that first wall, you’re going to suddenly see another one looming. It’s time to set a new goal, make a new plan, and start acting on it. There’s no time to sit on your laurels or sulk.

This is why I said, “If you set yourself up to be unhappy, even in success, none of the rest of this is going to be meaningful.”

Overcoming obstacles for a lifetime

I think five steps is a pretty good start for overcoming some of the bigger challenges you’ll face, professionally and personally. Everything hinges on setting those expectations and being willing to live with the results you generate.

That’s life, though. If you set out to do something, you should set out to do the thing that’s going to work best for you, not something that’s just going to make you miserable.

As I mention in the “Atomize” section above, this system parallels a few others you can find in development and project management. If you want a more refined, which is to say, “written in a book and 150 pages too long,” version of this, you can check out GTD or Pomodoro or any XYZ system.

To that end, Capterra offers some great resources that could help you get started:

If you’re stuck on the goal setting portion of the process, I recommend talking it through with someone not involved in the business directly. Accountants and software developers are my usual sounding boards—they think clearly and have a good eye for achievable goals.

Finally, get some support, while you’re at it. Any long trek can wear a person down, no matter how robust their business plan is. If you have someone to share the ride with, things will feel less horrific.

Heck, drop a line in the comments and make a new friend. Maybe you can take down Amazon together. Good luck.

Looking for Project Management software? Check out Capterra's list of the best Project Management software solutions.

About the Author

Andrew Marder

Andrew Marder

Andrew Marder is a former Capterra analyst.


Comment by Amna Sheikh on

Andrew Marder,
Also how can you find technical partner?


Comment by Amna Sheikh on

Andrew Marder,
What do one do when run out of budget for marketing in small business?


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