How to Bounce Back from Business Setbacks Fast: 5 Questions You Must Ask Yourself Immediately After a Setback

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A sudden loss of a major customer, a delayed shipment, an unexpected departure of your superstar employee, an injury/accident, a failed launch, a deal falling apart in the last minute, family emergencies… Operating a business comes with many unexpected challenges. Worse yet, multiple setbacks can come at us all at once.

When setbacks like these happen to you, they can take you right out of your element. This is particularly true when you are laser-focused on achieving your goal, leaving no room for doubts.


So, how do we bounce back from setbacks fast?


On a personal note, while writing this post, I experienced a setback. 

Only a few days from my meetup live event in NYC, I had no choice but to put it on hold due to an unexpected complication with the venue, where the event was supposed to be held.

This has never happened during my 2 years of running live events.  

If you are experienced in running events big or small, you know the production process starts way before the actual event.  You may also know that securing a venue is the biggest hurdle for anyone who wants to host a live business event. 

Needless to say, it was a blow at first.  To make the matter worse, in just one-weeks’ time surrounding this setback, I have gone through a massive water leak in my apartment, resulting in a section of the ceiling falling down and a family member getting injured.  Luckily, none of these were life threatening. 

Nonetheless, they did not help me get through a setback any easier.

This experience prompted me to write this post on how you can handle business setbacks better and faster.

At this point in my career, I can safely say that I'm a pro at dealing with setbacks because I've had so many in my life - both business and personal.  As I faced numerous setbacks, I have perfected a way to handle them better without forcing myself to believe everything is OK.

“Suck it up! It’ll be fine,” is something I would have said to myself when I was younger.  However, over time, I realized this was ineffective.  Pushing down your feelings about what happened can get you through tough times temporarily.  However, this is not a sustainable solution, as this can cause a burnout later, which would be a high price to pay.  

You often read or hear about how you should consider setbacks and failures as "opportunities."

I agree.  What I have noticed, though, is the lack of explanations out there as to how to genuinely feel like setbacks are your friend.  You can't force yourself to feel that way when you are mourning for your setbacks. 

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As you can see above, something has to happen in the middle between point A and B in order for us to truly feel like setbacks can bring new opportunities, so that we can roll up our sleeves and get to work with our minds in the right place.

In this post, I am about to share 5 questions that I always ask myself to help me bounce back from any type of setbacks.  And, you guessed it, these 5 questions act as a bridge between point A and B.



First Thing First - Do This 1 Thing Before Asking The 5 Questions

The beauty of entrepreneurship is to be given an opportunity to learn who you really are as a person and a leader.  What ticks you off, what gets you out of the bed every morning, and how you react to certain events are some clues that help you get to know yourself better.

Setbacks are no exceptions.  They offer a perfect learning opportunity to discover how you have been conditioned to handle them.  From there, you can formulate a way to manage them without putting too much emotional strain on yourself.

Before diving into these 5 questions, first study the thoughts that come to your mind immediately after learning about a setback.


Strangely enough, once you master the right way to handle setbacks, none of these, unless it is a life threatening situation, will come to you.  Instead, you will feel a sense of “relief.”  Frankly, that is exactly how I felt about a series of setbacks I recently experienced, although they all cost me time and resources in my business.                                                                  

Once you identify your thoughts and feelings about a setback, just acknowledge that these are there.  Don’t push them away forcefully or try ignoring them, as if those thoughts are not there.  Pretending that everything is fine will not let you move on any faster.  It is OK to take time to go over the feelings and thoughts that run through your mind.

One more thing: Ask these questions to yourself in this EXACT order.  I will explain why.

Now, it’s time to go over the 5 questions.


Question #1: "Isn’t this where most people give up?”

How do you feel about this question?  A little surprised to see this as the first one, I suppose. It is key to ask the question without paraphrasing.  Ask yourself exactly the way it’s written.

“Isn’t this where most people give up?”

Most of the time, the answer to this question is a loud, “Yes!”  The follow-up question that I ask myself after this is, “Am I one of those?”

Most of the time, the answer to this question is a loud, “No!”

To me, asking this question first out of all 5 questions gets me out of my funk, even if I am baffled by a setback.  It is because the question speaks to the deeply engraved entrepreneurial nature within us.  We are naturally more resilient than the rest of the pack, and we do not like to give up on things easily, unless there is mounting evidence not to move forward.

With this particular question, I am openly tricking myself into getting out of a pity party by provoking what runs in my vein – entrepreneurial resilience.  

Setbacks are NOT final.  Yes, it is not ideal, and yes, it would have been better off without it.  But, is this enough to stop you from what you decided to embark on? 

If you find yourself gradually backing out, this is a good time to assess how important it is for you to continue.  If it is important enough to you, but you feel like backing out, you need to know what kind of thoughts are holding you back.  It may be that you fear failure.  It may just be that a setback has shaken your confidence level. 

Clues can be found by the first thing I suggested you do before going through the 5 questions.  If you feel resentment, be honest and face it.  And ask why you feel that way.  Most likely the reasons are based on a loss of focus, time, money or other missed opportunities. 

Remember that you are not going to take them back by feeling negative.  Weigh your options out between backing out and regretting what you could have achieved by continuing on with your effort.


Question #2: "What opens up for me because of this?"

After you decide you are just not going to give up, this would be the next question to ask.  We can’t change what has already happened.  But, we always have a choice to look at it differently. 

In my case of a recent setback, it opened up loads of things.  Because, as of now, I am not sure when I can reschedule my event (and I decided not to care too much about it), this gave me a chance to work on many other things I consider important. 

In a sense, the way I understood the setback was that it was a sign to:


1.     Slow down from the constant grinding by having to go through some unexpected events

2.     Evaluate my priorities in my business, as I have a few projects going on

3.     Regroup by recharging now that I may clear my calendar for the rest of the year


This is the feeling of “relief” I was talking about earlier.  Let’s just say that there is a higher power whether you call it the universe or God or anything else, “it” knows my nature all too well.  I am pretty stubborn and determined to see through everything I set out to do.  Unless I get stopped by these “out of my control” incidents, nothing else will stop me. 

When these incidents got in my way, I was finally able to… pause.

Here is another example to use this question to your advantage.  Say, you have recently experienced a sudden loss of a major customer.  This is a huge blow to your business.  But instead of looking at it as a loss and fixating over it by letting your ego take over your mind, ask yourself what you can gain from it instead. 

If you are extremely honest with yourself, you will find some clues.  Maybe you were fed up with this customer, even though it was bringing in lots of business.  Maybe you have been exploring other options to hedge your risks by not relying on this particular customer.  And…maybe this is exactly what you needed to happen. 

At this point, if you can see new possibilities out of a rather hideous situation, you are well on your way to the final destination of considering your setbacks as the gifts that keep on giving.  What opens up for you counteracts with your negative emotions, so you no longer need to dwell on those thoughts you initially had.

Question #3: "Is this something I could have prevented?”

This is not to place blame on yourself.  Rather, this is an analytical question just so that you can have a sense of closure with your setback.

A setback is something that gets in your way to delay the progress of whatever you are working on, and often times, it is not something you expected to happen.  My case was no exception.

I would not have predicted that the massive water leak in my apt was inevitable.  There was nothing that suggested this was going to happen.  

I would not have been able to stop someone in my family from getting injured.  I wasn’t there, and even if I had been, I doubt I could have stopped it from happening.

I used the same venue 2 months back with no issues, and it actually was a great experience with everyone involved.  I had no reason to predict something would happen to force me to postpone the event.

All these things were out of my control. Double-checking these facts alone immediately gave me a sense of peace that there was no point of me feeling anything negative towards any of these incidents. 

Say, you have been working on a deal for the past 4 months straight.  Everything was going smoothly, but at the last minute, the other party backed out without any explanation.  Disappointed probably would be an understatement to describe how you feel. 

You may feel a sense of betrayal.  You may feel depressed over how much time was wasted.  This is the moment you ask this question of whether you would have been able to predict something like this, given all the data and experience you gathered over 4 months?  If your answer is no, then what is the point of feeling negative?

I know.  It is easier said than done, right?

Bear with me for a min.  I have been there a few times with something similar to this.  I still felt a sense of relief for not going through with those deals, because it would have been a lot messier if they fell apart once deals were signed.  It was better off that those deals did not go through. 

Another take on an incident like this is to look at it as a good practice to better prepare you for the real deal.  As difficult as it seems, these unpredictable setbacks are meant to happen to your advantage.


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Question #4: "How important is it to put this back on track the way I planned originally?"

Several years ago, on the outskirts of São Paulo, Brazil, I nearly died in the ocean because I was sucked into a rapid current while I was swimming.  I was drowning because I fought against it.  

Any surf pros and life guards recommend doing the exact opposite. 

“Don’t fight the current. The ocean will spit you out once you let go.”  I knew this before I got into this mess, but I did not trust the advice.  I truly believed if I let go, it would have taken me further away from the shore and I would not have been able to get back.  So, I decided to trust my ability to swim instead.  A bad idea.

Luckily, I was able to free myself by the sheer will of not wanting to die on my friend’s wedding day.  (Frankly, that’s all I thought about when I was struggling, as that would not be acceptable in my book.  Funny how I didn’t think for a second about just wanting to live.  This is a story for another time.)  Anyway, I was cutting it very close. 

This happened because I was a confident swimmer.  First, if I were a novice, then I would not have taken a chance to break away from the pack and swim further out where no one was around.  Second, because I am a good swimmer, I never thought something like this would happen to me. 

Complacency can act as an invitation to setbacks.  Food for thought…

In the end, I was completely exhausted to the point of nearly passing out.  If I chose to surrender to the current, I would have achieved the same outcome of staying alive & being back at the shore without nearly killing myself.  

After that experience, any decisions I make, I do not exclude an option of just “letting it go” instead of trying to manhandle and coerce the situation to my liking just for the sake of honoring what I set out to do.

To be clear, this is not the same as giving up.  The difference is to evaluate your approach to achieving your objective.  A setback can act as a reminder that, perhaps, you can reach the same outcome with less effort by choosing another method.

As for my event, I decided to postpone indefinitely until I am clear on how I want to continue offering these events.  After asking myself these 4 questions, it became clear to me that putting this back on the map immediately by scrambling to find another venue just for the sake of “making it happen” would not add any value. 


“Question #5: "What do I need to do immediately & what can wait?”

Normally, this is THE question most people ask first when a setback hits them in the face.  I see the temptation to immediately fix the problem at hand.  Here, I ask you to resist that urge. 

The main reason most people want to ask this question first is because it is an easy question to answer.  Also answers to this question are easily implementable.


“I need to get in touch with my lawyer.”

“I have to notify my vendor.”

“I need to post a job right now to find a replacement.”


These are knee-jerk reactions that will keep you busy so that you don’t have to answer question #1 through #4.  You can see that asking this question first will further delay your bounce-back process, and you might also miss a big “aha!” moment.

Only after you go through the first 4 questions, are you mentally ready to tackle these administrative matters. 

Of course, I had to take the various event related posts down from the internet indicating this event was canceled.  I also had to refund everyone.  Then I needed to notify the crew, including the guest speaker, with the bad news.  I did these tasks in order of urgency over 3 days.  I did not allow myself to work on all of them in one afternoon, although I could have. 

This is because I was not going to let this setback overtake all other matters…such as running my business as usual and attending an event I promised I would be at for someone.  After this self-questioning process, I was able to execute my administrative tasks one by one when I saw a pocket of time in a very calm manner. 

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The Bonus Bits: Enjoy the Xmas Effect

If you don’t celebrate Xmas, replace this with something you looked forward to each year as a child.  About a month or so leading up to Xmas day or any other occasions, you would recall your life was filled with the anticipation of that celebratory day, right?

You thought about how it would feel on that day, you talked to your friends and family about what was planned for you, and you may even have helped your parents or grandparents prepare for the occasion. 

Would you say that days leading up to the big day were more enjoyable than the actual day itself?  Once the day arrives, it is still exciting and fun, but nothing like those days of longing and anticipation for what you would experience on that day.  There is something magical about the days you count down. 

What does it have to do with bouncing back from setbacks?

This is a reminder that we often forget the joy of the journey to get to where we want to be in our business.  It is easy to be knocked down by sudden setbacks and let them be the biggest buzzkill.  Love the journey, not the destination, as you will never be able to experience the same journey twice.

That is why you should take a step back while you ask yourself these questions and see it as if your setback is part of a process leading up to something wonderful.   Not to mention, the more you do this, the faster you recover from any setbacks.  After a few times, you might just sit there and not even flinch.  You might even be able to smile and say, “Bring it on!”

Just to recap, all the 5 questions serve a purpose when they are put in this particular order. 

Question #1Redirect your mind from negative thoughts by resetting your focus back on who you are as an entrepreneur.

Question #2Continue redirecting your thoughts to shed some light on gains rather than losses.

Question #3:  Revisit your setback to assess whether it was preventable to have a sense of closure.

Question #4Explore & regroup by taking a step back.

Question #5Bring your attention to what tasks you need to do immediately.