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Overcoming Obstacles to Earning More: Beat Your Fear of Failure and the ‘Not Enough Time’ Excuse

You want to earn more money by starting a side hustle but you’re worried you don’t have the time and you’re afraid of rejection. How do you beat your fear of failure and overcome the oldest excuse in the book: “I don’t have the time”?

Overcoming obstaclesTwo weeks ago, I asked you – that if want to earn more money — what’s holding you back? Even if the path to a larger income is as simple as getting a weekend bartending gig or reaching out to existing contacts for freelancing work, we all have plenty of excuses for not taking action.

Your comments identified three things holding us back from earning more money that most of us shared:

  • “I don’t have enough time”
  • Fear of failure or rejection
  • Lack of ideas

I’m going to tackle the last one – finding side hustle ideas – next week. But before you focus on how you’ll earn extra money, you have to eliminate the factors that are holding you back.

I’ve learned a great deal in this area from Ramit Sethi of iwillteachyoutoberich.com. Ramit started out as a personal finance blogger like me but moved on to exclusively help readers maximize their income and productivity. I’m studying some of his materials right now to help with my own time management.For those interested in starting taking a side hustle to serious levels of income, he also offers an authoritative course called Earn1K that provides step-by-step tactics to grow your side hustle to $1,000 a month or more. More on that next week when we talk about side hustle ideas.

Right now, let’s focus on the roadblocks – or as Ramit would call them, barriers – that you said are holding you back from taking on a side hustle.

You said that you don’t have enough time.

“By the end of the day I don’t have much energy or time left.”

“I have a young child, and caring for him does take up a good deal of time… especially when you add in all the household chores that need doing.”

“What keeps me from having a side hustle is the lack of time.”

And that you’re afraid of rejection or afraid of failure.

“Fear: Fear of failure, of making mistakes, attracting the wrong clients, and ending up like all the other personal trainers I knew back home who barely scraped by from session to session.”

“The reason I haven’t put forth any energy into either of those has been mainly because of fear. What if it doesn’t work.”

“What’s holding me back is my fear of rejection and care for my daughter but if I want it bad enough I will find a way.”

Again, we’ll look at finding ideas for your side hustle next week. Right now, let’s tackle the first two roadblocks: Fear of rejection or failure and a lack of time.

How to beat your fear of failure and rejection

A fear of rejection and fear of failure are different but related. A rejection is a tiny failure: Your boss says “no” to a raise, your prospect says “no” to a sale. Failure only comes after repeated rejections. Let’s take them one at a time.

Nobody likes rejection. In any situation where we’re asking for something – for a sale, for a date, for a job, for a raise, we’re going to be anxious about the outcome. That they’ll say “no”. That’s natural. But there’s a difference between being anxious about asking for what you want and being so anxious that you never ask. You never try.

I know first-hand how a fear of rejection can derail someone who might otherwise be successful…me!

I don’t write about it very often, but I’m an anxious guy. If I’m not careful, I can spend all day worrying about the potential outcome of an upcoming meeting or conversation. I have to push myself to go to social events (though I’m always glad I go). And when it comes to making phone calls, well, forget about it. If I didn’t work at it, these phobias would make my life suck. But instead of letting them beat me, I push through them and have the meetings and go to the parties.

There’s some things I still struggle with, like making important phone calls. For some reason, to me. the telephone is the most terrible, anxiety-inducing device of torture ever invented. And to my horror, my career somehow steered me — not once but twice- –  into jobs that involved a great deal of telephone sales.

And get this: I failed at those jobs. Yes, I failed! I wasn’t just rejected a time or two, I failed after many months. Not because I was rejected too many times, but because I gave up. I said “I don’t want to do this anymore.”

But you know what? That’s OK. I’m better because I failed. I moved on to do things that I enjoy and excel at, like blogging, that I might not have found if I had stayed at my old jobs.

Everyone feels anxious from time to time; not everybody needs a therapist. Everyone gets rejected from time to time, but that doesn’t automatically lead to a failure. But even if it does, we all need to fail, too.

Knowing that rejection and failure are a part of life and business isn’t enough for everybody, I know. So you can work on your fear of rejection or a fear of failure by doing three things:

1. Ask yourself: What are you actually afraid of?

What’s the worst that will happen? Someone will say “no”? You’ll annoy someone?

Then ask yourself: Is it rational? It might not be: For example, that your boss would fire you for asking for a raise.

Finally, ask yourself: Is it harmful? It’s hard to justify your fear when even the worst potential outcome isn’t going to have a serious negative impact on your life or career.

2. Accept that the more you fail, the more you succeed.

This is cliché advice, isn’t it? We’ve all heard the infinite variations of “you can’t win if you don’t play.” But when it comes to earning more money, it’s some of the most important advice you can follow. You just have to keep trying things. We hear about successful people after they’re successful: “Bill Gates, Richard Branson, Warren Buffet, Steve Jobs”. But we don’t hear about the failures they endured getting to where they were.

I have a quote on my laptop’s background: “If you never failed, you never tried anything new.” Accept the fact that you will fail. Embrace it.

3. Just do it.

In my opinion, Nike has history’s best slogan – full stop. Just do it. Whatever it is you’re scared of, whatever it is you want to do but something is holding you back, just do it. (This is, incidentally, also one of psychologists’ recommended ways to beat most rejection anxiety.)

Just do it before your stupid human brain gets in the way. Just do it before you make excuses.

This could be said of running or reaching out to potential clients for your side hustle.

Just do it.

Then, do it often, because the more often you fail, the more often you’ll succeed.

A word about risk

Some readers mentioned the risks involved in starting their side hustle, primarily where capital was required to get it off the ground.

Certainly, a fear of failure is more tangible when it’s entangled with a fear of losing money. At the risk of oversimplifying this issue, consider that:

  1. As an entrepreneur, you will one day become so passionate about the right idea you will stop worrying about the money you’re risking. Until you feel that passion, maybe it’s the wrong idea.
  2. Most side hustles should not need much start-up capital. If you’re uncomfortable putting money at risk, find an idea that doesn’t require so much.

How to overcome the “not enough time” excuse

Technology allows us to do more in less time, but rather than take less time to do more, we take more time to do more stuff.

Right? Who here hasn’t taken two hours to do a 30-minute task because we’ve been texting, emailing and checking Facebook in between?

And who here isn’t guilty of flopping on the couch at 8pm to watch old shows on Netflix instead of learning something new/exercising/working on your side hustle.

Years ago, wine and social marketing guru Gary Vaynerchuck summed up the answer to “not enough time” excuse perfectly: “You don’t have enough time? Stop watching fucking Lost!”

So for many of us, there are hours in our day we can poach, but we’d often rather veg after a long workday than hustle.

There are two good strategies to tackle this:

1. For a week, keep track of how you spend your time in a spreadsheet.

Be brutally honest. If you wasted an hour on reddit, put it down. When you’re done, categorize and tally your hours.

Now, decide what’s important…and what’s not. Obviously, some things are unequivocally important…our day job tasks, eating meals, exercising and sleeping (to a point).

We also need some relaxation time, but it helps if it’s scheduled, conscious relaxation time. What I mean by that is that you say you’re going to read a book or go for a walk at this time rather than simply flopping on the couch and watching pointless reality shows just because you’re tired.

What about everything else? Do you need to play Candy Crush or sleep for 10 hours a night? Maybe not.

2. Eliminate unproductive time and set aside blocks for working on your side hustle.

Put it on your calendar. Even if you’re just looking/exploring ideas right now, and even if it’s just a couple hours a week; the point is to make it a habit just like going to work, brushing your teeth, or going to bed.

What if you’re still strapped for time? What if you have kids?

Some of us are more time-pressed than others, and this exercise may still not uncover enough meaningful time to work with. For example, you already work 70 hours a week or you have kids and, consequently, work 168 hours a week.

Does this mean that you can’t do a side hustle? Not necessarily, but you may have to rethink the kinds of projects you target. We’ll address ideas next time, but as a couple of thoughts to get you started: If you have kids, can you provide a service for other parents where you don’t have to be apart from your kids? (In home babysitting is the boring option, but you can easily spice this up – for example, mom (or dad) and me exercise classes on Saturday mornings.

If you’re so time-strapped that setting aside a few hours seems impossible BUT you’re not earning as much money as you want, you’re not extracting the maximum value for your time. In other words, it’s not a side-hustle you need, but a higher paying job (or at least one that pays the same for less hours, so you can focus on a side hustle!)

As you prepare to get a side hustle, remember two things:

  1. If it’s earning more money is a priority, you can make the time – either by replacing unproductive hours or finding higher-value work.
  2. To some degree, we all fear failure. But failing is an inevitable part of the process. Get out there and do it. Your anxiety will diminish and – eventually – you’ll succeed.

Next week we’ll talk about where to look for side hustles and how to formulate winning freelance/business ideas.

Let me know in a comment: What steps will you take THIS WEEK to beat your fear of failure or improve your time management so you can focus on building your side hustle?

Published or updated on January 30, 2014

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About David Weliver

David Weliver is the founding editor of Money Under 30. He's a cited authority on personal finance and the unique money issues we face during our first two decades as adults. He lives in Maine with his wife and two children.


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  1. Anna says:

    This article makes so many great points, and especially the part about making time in our lives. I think the excuse of “I don’t have enough time” is something people say to provide validity to the fact that they a) don’t have enough money and b) want to complain about it. No one will ever have enough time or enough money — there is someone else who always has more leisure time and definitely someone else who always has more money than you. Making the conscious effort to stop excusing your current monetary situation with the “I don’t have enough time” mantra will make you take control of your reality, time and eventually money. If it means that much to you, you’ll find the time.

  2. Jesse says:

    Exceptional article for this week of my life! My wife and I have been discussing turning a side hustle into full time work and implementing a couple other side hustles. It has been a rollercoaster between exhilarating and pain-in-the-chest stressful …especially for some one who loves a sure thing and is terrified of failure. Thank you for the reminder that leaving security and exposing myself to some degree of almost certain failure is the only way to achieve great success!!

  3. Jessica says:

    This is a great article! My husband and I really want to focus on paying down debt and saving for another child in the next 2 years. I work as an Account Manager for an EHR vendor during my full-time work, but also have social work and real estate licenses. Due to this, I work 1 hour a week ($50/hour) teaching life skills to a young woman with Asperger’s and an additional 10 hours a week ($30/hour) (7 remotely during the week and 3 in the office on Saturday) helping two real estate agents during the busy season. Both of these additional streams of income bring in around $1,000 a month, which allows us to achieve our goals. Luckily, my husband has an extremely flexible schedule and can be available to help with our son while I take on the additional streams of income. I think it is important for you and your partner to be on the same page and since we know this is a short-term goal that we are saving for, I think it makes things easier to stay on track and remain motivated.

  4. KA says:

    Great post (and previous one too). This week I’m working on getting my business license — I’ve been putting it off because I was just thinking what I’m doing right now won’t work out in the long term, it costs money that I’m worried about using for something that may fail, and a license isn’t “required” — but then I realized that it will open more doors with being more ‘legit’ — so now working on crossing off items on my list.

    I read something that was published awhile ago, and may have been repeated in the previous one: it’s easier to have multiple jobs when you’re younger and without children — that helped put things into better prospective. I’m doing well financially, contribute fully to a Roth IRA, etc, but probably wouldn’t have been able to afford private/parochial school for potential children on the future if I just kept my routine now, but now I have increased the side-hustle and money each month goes into a ‘potential child fund’ to help with future child expenses in the hopes that there can be more flexibility with life, lifestyle and retirement in the future.

    Another thing that I’m looking to incorporate and shows some creativity (I hope) with the “I don’t have time” crowd: I like to walk as a way of staying in shape. Cheaper than a gym membership. I’m now trying to find some dog owners in my neighborhood that would like a reliable and rather economical dog walker for specific times (the times that I walk). It’s a win-win for both the owner, dog and me; I don’t have to modify my life all that much to do something that I was already doing.

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