Are You Afraid to Take the Leap?

Impala AdeFrias

“Don’t fear failure so much that you refuse to try new things. The saddest summary of life contains three descriptions: could have, might have, and should have.” – Louise E. Boone

Impalas are majestic creatures that can leap as high as 10 feet in the air, and in one leap can travel 30 feet. That’s amazing! However, in captivity, when the impala is kept behind a fence that is only 3 feet high, it will not escape. Why? The reason is that their inability to see where they’ll land prevents them from making that leap.

I really enjoy watching Shark Tank, and I love the entrepreneurial spirit and passion of those who come on the show. Many of them left their jobs to devote their life to something they believe in. I truly admire those who were willing to take that leap in their career by leaving their jobs to do something they are more passionate about. J. Money from Budgets are Sexy and Holly and Greg from Club Thrifty took the leap and have successful blog(s) as well as other online businesses. Likewise, Shannon from Financially Blonde, left her job in Wealth Management to start her own company. She also wrote a blog post recently saying that she urges her mentees to be brave and to not fear the gap. Leaving a steady paycheck and working for yourself no doubt takes a big leap of faith. I haven’t yet found something that I’m passionate about which would also earn me an income, and my blog probably made less money in its almost 2 years in existence than I probably make in one day in my regular job. Though I know that working another 20 years at my current job is not something I see myself doing. But even if I find my passion, I question whether I’d have the courage to leave a steady paycheck and benefits.

I also admire those who were able to save up enough money to call it quits and leave the workforce at the prime of their earning years because they’ve decided there are better things to do with life than working until you’re 65. Justin from Root of Good quit his job at 33 and spends much of his time relaxing, learning new things, and spending time with his family. Jeremy and Winnie from Go Curry Cracker left their jobs in their 30s to travel the world. Who doesn’t want to have more time to do the things they want to do, to spend more time with their family, to learn new things, and to travel more. While I am no where near taking the leap into early retirement or early financial independence, I know that even if was, I’d be worried whether the money would last and what others would say about such an audacious plan.

Never let your fears get in the way of your dreams

In high school, my sister bought me a t-shirt that said “Never Let your fears get in the way of your dreams.” Those words inspired me and they appear next to my picture in my high school yearbook. I was young and the world was my oyster. Anything was possible! I could accomplish anything if I put my mind to it. Sometimes I miss the enthusiasm and confidence of youth. Although, I was always optimistic about the future at that age, I was also always risk averse and still am.

I am sure many of those who have taken that leap into the unknown have moments of panic and experiences of failure. Ultimately, no one has a crystal ball to see into the future. You do your research and your due diligence. You take calculated risks, but you take that leap. YOU TAKE THAT LEAP. Too often, many of us, myself included, will succumb to analysis paralysis where we overthink things and never do anything. Planning and being prepared is a good thing. But never taking action is not. So stop doubting yourself and do what it is that you know deep inside you were meant to do. Don’t worry if you fail. There are no failures in life, only life lessons. Doubt kills more dreams than failure ever will. “In the end, we only regret the chances we didn’t take, relationships we were afraid to have and the decisions we waited too long to make.”

What’s holding you back from taking that leap?

62 thoughts on “Are You Afraid to Take the Leap?

  1. Shannon @ Financially Blonde

    “Never Let your fears get in the way of your dreams.” I LOVE this quote!!! Obviously these are words that I live by, and it’s absolutely scary and terrifying to make a leap into an unknown, but from my perspective, it’s scarier to not, especially when you have a true passion for something. It’s not easy to start something on your own, but your passion helps you get through those tough times. Thanks for mentioning my post!!
    Shannon @ Financially Blonde recently posted…Hard Work Sucks But Quitting Sucks HarderMy Profile

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  2. Retired To Win

    I’ve taken that leap into the unknown of a new business venture a few times. Sometimes I’ve landed on my feet and running, and sometimes I’ve landed on my face. But you’re right that you should not live wondering what might have been. (At least, I haven’t.)

    But, for me, leaping into earlier retirement did not carry that same feeling of uncertainty. If you’ve made a good plan and have executed it properly there’s really not much uncertainty involved. Of course, I say that having hedged my bet pretty heavily by gradually gearing down my basic living expenses so that my passive income covers them three-fold. Lots of wiggle room there. But (IMHO) that is part of having a good plan that strips away most if not all of the uncertainty.
    Retired To Win recently posted…How Frugality Has Bought Me TimeMy Profile

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    1. livingrichcheaply@gmail.com Post author

      Interesting, what kind of business ventures? You’re right, I can see how early retirement is not as frightening if you have a good plan. But when it’s extreme early retirement, it does bring more uncertainty.

      Reply
  3. Broke Millennial

    “Remember who you wanted to be.” I wear a bangle on my left wrist everyday with that saying. My Mom gave it to me the day she dropped me off at college in 2007 and while the career I’ve wanted has changed in over 7 years, the type of person and long-term dreams have remained the same.

    Thanks for a great post to remind us all to take a little risk.
    Broke Millennial recently posted…Frugal Find Friday: Digit (The New Way to Save)My Profile

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    1. livingrichcheaply@gmail.com Post author

      That’s great…I probably need a reminder too! Thanks for the compliment…I think it was written partly to inspire others to take that leap, but also to remind myself as well.

      Reply
  4. Justin @ Root of Good

    Well said! Thanks for linking to a little taste of what I’m up to in early retirement. :)

    I guess I took a leap into early retirement. I got let go from my former employer and decided we had “enough” to be FI and so I called it early retirement. So far so good, and even if I have to go back to work some day, this multi-year break has been pretty freaking sweet!
    Justin @ Root of Good recently posted…Cost Effective Investing With MotifMy Profile

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    1. livingrichcheaply@gmail.com Post author

      Yea, you’re living the life Justin! I wish I had learned about early FI when I was younger…but it’s never too late.

      Reply
    1. livingrichcheaply@gmail.com Post author

      I know the feeling. Deep inside we often know that we need to make that leap. The fear is sometimes not rational.

      Reply
  5. Gen Y Finance Guy

    The biggest thing holding me back from taking the leap is the golden handcuffs. When you are making 6-figures at a pretty cushy corporate job its hard to leave. But I will continue to work on my side-hustles and eventually will find one to turn into my main hustle.

    I won’t make the jump until I am confident I have as much if not more upside in that I currently have. Or until I hit my number.

    For now I travel down two paths…perfecting the blend until I can muster the courage to make the break.
    Gen Y Finance Guy recently posted…My Love/Hate Relationship with Tax SeasonMy Profile

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    1. livingrichcheaply@gmail.com Post author

      I feel the same way. It is hard to leave when you have a good paying job and great benefits. It would definitely make it easier if I had a side hustle or something income-producing activity which I enjoy doing that I could do in earlier retirement.

      Reply
    1. livingrichcheaply@gmail.com Post author

      Very true. And it’s tougher when you have a family too. When you’re single, you’re only putting yourself at risk.

      Reply
  6. Joe Saul-Sehy

    My favorite quote is an old one that Nike used before “Just Do It.” It’s “Feel the fear and do it anyway.” I always feel fear and have to continually remind myself to go ahead and leap. It helped me sell my business, start my first blog, start the podcast, run a marathon, ask my wife to marry me, buy a house…..and on and on….”
    Joe Saul-Sehy recently posted…Nicole Lapin Makes Us All Rich BitchesMy Profile

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    1. livingrichcheaply@gmail.com Post author

      Yea I like that tagline. People who make the leap and are successful often feel the fear…but they still make that leap. Glad you made the leap on those…you’re rockin’ it!

      Reply
  7. Abigail @ipickuppennies

    My husband is on disability, so I’m the only real wage earner in the house. Meanwhile, we also both have health problems that a) inhibit our ability to do things, including many frugal hacks and b) make our lives expensive.

    That’s enough to make me very, very afraid of most things financially. I’m sure I’ve missed out on some opportunities, but I’ve kept myself and my husband (and now my in-laws) safe and housed. So I guess that’s the best I can do.
    Abigail @ipickuppennies recently posted…Can we save $10,000 in 7 months?My Profile

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    1. livingrichcheaply@gmail.com Post author

      Sorry to hear that Abigail. We can’t control our circumstances, we just have to make the best out of the cards we are dealt. If it’s the best you can do…that’s good enough.

      Reply
  8. Income Surfer

    Nicely put Andrew. I inherited far too many fears from my father……and have been working hard to overcome them most of my life. It’s crazy what we could each achieve if we just tried…..and proceeded on faith :o)
    -Bryan
    Income Surfer recently posted…One Month HiatusMy Profile

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    1. livingrichcheaply@gmail.com Post author

      I think I inherited that trait from my father as well. He was not a risk taker and was pretty risk averse.

      Reply
  9. Tonya@Budget and the Beach

    Actually nothing has been holding me back lately! I’ve been going for it. And while the temptation is there to want to give up and just look for a full time job, I think about how I’d be letting myself down in the long run. There is, or probably will be some struggle if you do take the leap, but there is also a lot of freedom and pride to know you are doing what so many people are afraid to do.
    Tonya@Budget and the Beach recently posted…Following My Passion for Storytelling!My Profile

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    1. livingrichcheaply@gmail.com Post author

      That’s great Tonya…you really are going for it and I admire you for that. Good luck with it! You should feel a sense of pride that you took a leap that others may be too afraid to make.

      Reply
  10. Mrs. Maroon

    Oooh, I succumb to analysis paralysis often. Even about silly, meaningless stuff. So the big stuff can be really hard. The funny part is that I’m super confident in our plans for early retirement. I’d be a nervous wreck if we were trying to start a business right now, and needing to rely on it for living expenses. But the prospect of early retirement feels like a breeze to me. Perhaps maybe just because its several years down the road. I might become a basket case as it approaches. That’s what I have Mr. Maroon for… he helps to keep me grounded. And nudges me towards that leap!
    Mrs. Maroon recently posted…Don’t Treat Diet Like a Four-Letter Word – Same Goes for BudgetMy Profile

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    1. livingrichcheaply@gmail.com Post author

      Yea, I over think small things to! I’m somewhat confident with our plans for early retirement but it’s tough because we’re in a high cost of living area. Plus, there’s the big pension payoff if I stay longer which is my golden handcuffs. It’s great that you and Mr. Maroon are there to encourage each other.

      Reply
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  12. Jason

    I think this is a good question that I think about a bit even though I am not even closed to FI. For me, I think the big thing is: 1) worry about the money running out; 2) what would I do with my time. I don’t know if I would start my own business or something. I mean I have over 25 years of teaching public speaking and could become a coach. But I am lulled by the steady paycheck, the intellectual stimulation from my job, etc. I wonder if/when I can and will take the plunge.

    Any advice?
    Jason recently posted…How to Strike A Balance Between Wants and Needs to Achieve Financial DreamsMy Profile

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    1. livingrichcheaply@gmail.com Post author

      I have the same questions. But I think for those who have reached FI, it’s a purely mathematical equation. The general rule is a 4% withdrawal rate so determine how much your expenses will be and figure out how much money you need. As for what you would do with your time, I think only you can answer that question. Is there something you’re passionate about or interested in doing, but can’t because you don’t have the time? Traveling is often tops on the list. If you enjoy your job and the intellectual stimulation, maybe there’s no need to leave. Or maybe you can find something else that provides that intellectual stimulation.

      Reply
    1. livingrichcheaply@gmail.com Post author

      Unfortunately, it seems like the older we get we risk losing the passion we had when we were younger. You’re right, sometimes if you find others to similar interests and goals who are aggressively pursuing those passions, you’ll find that passion you had.

      Reply
  13. Felix Money

    I would love to soon quit my job, but it’s really scary. The money is good, but I feel I can’t do it for much longer. I bought a business last week, but it is scary to survive just from that income, since it seems to be so unstable and could easily go south, and have a couple of rentals, but the income is minimal. I was thinking to maybe buy 2 more rentals and one more business, and then quit. The income from the rentals combined with my spouses income should cover expenses, and if the businesses don’t fail, we could use that income for saving or reinvesting. Anyway, that’s my ‘big’ plan, but I don’t know yet if I’ll have the courage to do it.
    Felix Money recently posted…Illegitimi Non Carborundum – How To Keep On Keepin’ OnMy Profile

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    1. livingrichcheaply@gmail.com Post author

      Hey Felix, I remember reading your post about the conditions of your job. In your situation, I may be more inclined to take a leap because your health is a priority. Obviously, you have to have your ducks in a row before you leave.

      Reply
  14. DC @ Young Adult Money

    Excellent point about people leaving the workforce during their prime earnings years. That’s the thing that’s really getting to me lately. Even if I had a successful business plan, I think I would absolutely try to do it 100% on the side. I just can’t imagine giving up a great job at a great company and leaving a career track that will likely pay even higher salaries if I just stick to the path. I think it’s important to note that there is some bias when reading about people taking the plunge. Of course we are going to hear about people’s successes – everyone who succeeds wants to share it with the world. On the flip side those who take a risk and fail typically will not share their thoughts. The takeaway is to be cautiously optimistic with everything and to have a solid plan in place
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    1. Felix Money

      I agree with you, DC, having a great job leads to a much higher opportunity cost if you quit that job and take the risk of running your own business/businesses. I personally have a job that pays good enough money (not great) , but there’s no more upside to it and it’s very physically and mentally taxing for me. Therefore, I would rather either take a chance with businesses or if that doesn’t work out, maybe take a part-time job that enjoy and learn to live on less.
      Felix Money recently posted…Illegitimi Non Carborundum – How To Keep On Keepin’ OnMy Profile

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    2. livingrichcheaply@gmail.com Post author

      I know what you mean, but sometimes to be successful, you have to put 100% into it and that may mean leaving your job. I guess if you’re happy with your job and career track then the decision is more difficult, but if you’re burnt out or want to transition to something else…higher salaries aren’t going to keep you around.

      Reply
      1. DC @ Young Adult Money

        That’s totally fair, but I think a dislike for your job is actually a really bad reason to start a business. I wrote a couple of posts that shared 4 bad reasons to quit your job and start a small business, and a dislike for your job is one of them. It forces your business plan to be influenced too much by emotion. You need to really be thinking clearly and logically if you are going to quit a job to start a business, and disliking your job can heavily influence you in a negative way.

        I feel pretty strongly about this if you can’t tell, but I’ve also spent a ridiculous amount of time weighing the pros and cons of starting your own biz.
        DC @ Young Adult Money recently posted…3 Ways to Make Your Living Situation More AffordableMy Profile

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        1. livingrichcheaply@gmail.com Post author

          Yes, I can you feel strongly about this! I agree with you though. You shouldn’t quit your job just because you dislike and start a business without much planning. I think having the business start off as a “side hustle” or a part-time gig is a great way to learn whether you really want to do that and whether you think you can produce income to replace the income you’d lose if you were to quit. The grass is always greener on the other side. Being your own boss of your own business doesn’t automatically mean you won’t dislike that job. So testing it out on the side is always a good thing. What I meant about disliking a job is that if you dislike your job it often gives you more motivation to figure a side hustle and then eventually take the leap if you’ve determined that it will likely work, not blindly jumping into it.

          Reply
          1. DC @ Young Adult Money

            Great point and I agree: if you dislike your job you are definitely more motivated to start something on the side. As we both know, doing something on the side like blogging or any other business isn’t easy. I would say blogging is a fairly easy side business, too, because you can neglect it a bit without the business going down the crapper or losing a client (some may disagree with this assessment, but I compare it to a side hustle like IT consulting where you really need to meet the client on their timeframe).
            DC @ Young Adult Money recently posted…3 Ways to Make Your Living Situation More AffordableMy Profile

  15. Shannon @ The Heavy Purse

    Love this, Andrew. And what a great quote from Boone. I ‘m not afraid to take the leap but sometime I do over think things first. :) It really helps having a partner that is so encouraging and supportive. Chris definitely believes I can leap 10 feet off the ground too. And you know what – sometimes I can even leap higher. But you don’t know until you try! :)
    Shannon @ The Heavy Purse recently posted…Crazy Tax Deductions #InfographicMy Profile

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    1. livingrichcheaply@gmail.com Post author

      I envy those who are doing what they’re passionate about and helping others too! It’s always great to have someone who supports you and believes in you. It really is a great asset to have.

      Reply
  16. Erin @ Journey to Saving

    Analysis paralysis can be my biggest enemy. I’m all about researching things to death, even after I have all the necessary information. However, I wouldn’t say I was scared when I quit my job and moved. I knew my emergency fund would keep us afloat in the worst case scenario, and the fact my fiancé had a steady job helped, too. I’m immensely grateful I “took the leap” even if it didn’t feel like I actually took one. I’ve learned a lot and have become less fearful because of it. I don’t want to have any regrets!
    Erin @ Journey to Saving recently posted…Being Grateful: Fifty-Eighth EditionMy Profile

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    1. livingrichcheaply@gmail.com Post author

      Yes, I think this is a personality trait that we share. I also research things to death. I’m glad that you took the leap as well and it appears that you are doing well so that’s wonderful!

      Reply
  17. Done by Forty

    We have one big leap coming up in the next five years or so. I often wonder if I’ll have the guts to make it happen.

    I’m naturally risk averse and typically tell people not to take leaps. I may be doing them a disservice but honestly believe that success is often just a string of steady gains, over the years, while avoiding the big pitfalls. Leaps involve risk and are therefore dangerous.

    Of course, there’s a downside to playing it safe, too.
    Done by Forty recently posted…The Full CostMy Profile

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    1. livingrichcheaply@gmail.com Post author

      Your done by 40 right?! Man I wish I could take that leap too, but I don’t know if I can do it here in NYC. I think if we moved to a lower cost area though… I like what you said about success being a string of steady gains over the years. Often times that’s how success is built, not from one “leap”…it just sounds more exciting I guess.

      Reply
  18. EL @ Moneywatch101

    I think we all have that little bit of fear of the unknown. If you prepare and plan on how to exit the workforce, IM sure it will make the transition a bit easier. I like when you take a risk you come away with a lesson no matter the outcome. I am always learning and taking risks. Good luck in 2015.
    EL @ Moneywatch101 recently posted…Money TalkMy Profile

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  19. Mihai

    I guess we are simply not prepared to take the leap. Just like the impala behind a wall. It takes some courage to go where you have no idea what’s waiting for you. It may be good, it may be bad, we are simply not prepared for it.

    Reply
    1. livingrichcheaply@gmail.com Post author

      If you’re not prepared, it’s probably best not to make that leap yet. It’s when you’re prepared and all signs point to making the leap, but you still hold back from taking the leap is where the problem lies.

      Reply
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