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Owning a Side Business Will Boost Your Office Confidence at Work

Only those who have experienced the bliss can relate to how and why a side business can boost one’s confidence at work.

My wife and I were chatting last night trying to plan our next international vacation.  I had found several good packages online but could not commit to any because my wife was concerned about her work.

She was concerned because she has been maxing out all her personal time off and has taken several unpaid leaves (She is the only one who has been able to do this because she is such a Superstar).  Not your average employee by any means.  I keep telling her that she doesn’t have to work, but she loves what she does.

I also keep telling her that it is ok if they let her go because there will be several others willing to pick her back up.   She is the top salesperson in the entire North American sub continent of a multi-billion dollar company based in Europe. What does she have to worry about?

Obviously that is only my perspective.  Her perspective is influenced by several layoffs recently at her company, and the announcement that more are to come.  Whether she is consciously aware of it or not, I am positive that some type of fear (even the slightest) caused by an external circumstance beyond her control is influencing at least part of her psyche or thought process.

My Days in Corporate America – A Flash Back

Our discussion reminded me of how I was when I first started in Corporate America.

I remember in the office, everyone used to put on their game face and displayed their enthusiasm for what they did whether or not they were killing their soul.

Let alone the actual task on hand, everyone focused on “building relationships”, making sure they are around the water cooler to converse with Jane and the first to reply to all corporate gatherings and get together emails. I did too.

Everyone wanted to get in before the boss and leave after, whether or not they got more done is irrelevant, but face time certainly wasn’t. It was all about the bosses, making sure they are pleased with everything, from the way you work, dress, smile, eat, sleep and probably breathe. I did this too and felt like a looser that I was.

Everyone worried very much about office politics, who is in with who, and which boss likes who. From associates to Directors and even higher, it was interesting to observe the nature of office politics and what it can do to a man (or woman). When it came to brown nosing, there was no difference between me, and Intern and a Senior Director. We all looked pathetic in the exact same way.

Because staying ahead in the political landscape meant keeping the bosses happy, one did anything and everything to please the boss. The word NO (pushback) didn’t exist. I too was part of this.  Young, ambitious, confident, highly qualified college grad ready to take on the world.

What I did find however is that even those with confidence at work had to tame down in front of the bosses. I quickly learned that in my profession, confidence at work came with position and tenure.  The person behind the position may not be worth a penny from a confidence perspective, but in the office he or she was the lion and the subordinates were the sheep.

It wasn’t uncommon to hear meek subordinates respond “I don’t know” or “I am sorry” with a sheepish grin. Again, I was part of the parcel too.  Boy do I not miss them days.

Unpredictable External Forces

When you work for someone, you are at their mercy. Sure you can argue that you are a born Superstar, extremely dedicated and hard working, are the best at what you do and proactively work to network and grow your career at all times, but so what?

You may be saved 99 times but what about that 1 possible time when the ax swings because the swinger has no other option?  It’s dog eat dog out there and it’s either their head or yours. So what gives? Can you predict the future? DO you know what will happen to your company tomorrow? Or what the owner may decide to do?

Sure you may argue that because you are a Superstar that you can reach out to your network or apply somewhere and find another gig relatively quickly. But can you really? Can you control the market forces? Can you control other human beings, their motives, how they think and what they do? How the economy works? What direction the country is going in?

Or you may be religious and say that when one door closes, several others open. But do they? And if they do, do they fast enough? Externalities or outside forces is what I am getting at here. The bottom line is, no matter who you are, how good you are at what you do, or what you think, there is always a point during which none of that matters.

We cannot control externalities. No one can. It’s a simple fact of life, and the sooner we come to terms with it the better for us.

Focus On What You Can Control Instead

There are many things that you cannot control that impact your life.  But there are also some things that are completely in your control if you want to reduce the risk or exposure that can be caused by externalities.

When I was working for a paycheck, I was completely dependent solely on that paycheck for my livelihood.  Without the paycheck, I wouldn’t have been able to pay my bills and save for the future.  I would argue most people are in this situation.

I consider myself fortunate to have realized this cause and effect relationship early in life, and as a result had plenty of time to ponder over how best to reduce reliance on just one income stream.  This is part of the reason I decided to pursue a side business despite having a high paying corporate career.

It was one of the best decisions I have made in my life, one that benefited me in more ways than just tangible, and which propelled both my career in Corporate America and my self-started career in entrepreneurship that has gotten me to where I am today.

Starting a business allowed me to reduce my reliance on the paycheck by diversifying my income streams.  It also provided a safety net to fall back to in the event of an unforeseen circumstance such as job loss.

It also increased peace of mind in that I knew that I wouldn’t get bored out of my mind sitting at home in the event I had no work and that I had something to look forward to.  There are countless other benefits that I enjoyed, but none greater at the time than the immediate benefit of career growth.

Over the years, one side business led to another and so forth, and I was able to acquire more skills and confidence at work in the process that my career would not have been able to give me alone, at least in the earlier stages.

All the physical, mental and emotional benefits of running side business(es) resulted in more self confidence at work which I could and would actually display, not nearly caring as much as I would have previously about the effect it might have on my career. A big reason is knowing I had something that I could fall back to.

It was almost as if I developed this I don’t give a crap about you attitude toward the boss. I don’t mean this as a personal attack. All I am saying is that I didn’t care about the formalities and brown nosing.

My activities outside work made me realized my value and what / how I was contributing to the firm, and that reflected in my attitude, speech and behavior.  I am convinced there were many smarter than I at the firm, but because of that slight fear in the back of their minds which I mentioned above, I am sure that many were not able to display or convey their value in a similar manner.

That’s when I started realizing the transformation I was going through and how it reflected in my career progression. I became a bigger, stronger, bolder, brasher and faster Rat in the race.  I became Super Rat.  I am certainly not recommending one deliberately behaves how I did. I am simply sharing my personal experiences.

But was there real tangible change in the workplace of was it all just in my head? I would argue the latter is the case.  It’s the human psychology factor that propelled my career, all thanks to my side businesses.

The Human Psychology Factor

Why Psychology? Even after gaining all kinds of experiences my career would not have taught me so early, I wasn’t all of a sudden smarter or better in my profession.  I worked just as hard as I did before, and the quality of my work was just as good.

What was different however is the way I perceived externalities.  I simply stopped caring about them, and as foolish as I was (or am), I truly believed that I had full control over them rather than the other way around. Why? Because I was no longer dependent on them. I was diversified enough to care less.

As a result, the way I spoke, behaved, walked, acted, or anything else for that matter changed. The change started getting me noticed more.  Was the change deliberately planned and implemented? No, I can’t take credit for the transformation. It was a result of what I was doing outside of work.

Many are talented enough to condition their mind to plant seeds of success.  But I didn’t have to do this.  My businesses were getting established, and I could see a brighter light each day at the end of the tunnel.

I am sure you can relate to me when I say that even a mere $100 earned from your website or blog that you run on the side gives much more pleasure than the $1,000 earned at work doesn’t it?  The feeling is even better when the $100 grows to $200.  Emotions start getting out of hand when you reach $500.

Why is that the case?  Because our mind knows that the paycheck from work is a given.  It’s really not but that’s what we become programmed to think. It’s fixed income that we have come to start expecting.  That is how we run our household on a day to day basis, hence the concept of budgeting.

But is income from a side gig a given? Not at all either, but we would like it to be. So we end up working longer and harder for it. And because we choose what we do, we enjoy that work and don’t feel like we are working. Remember that many people don’t like what they do.

When our side work results in income, we get the fruits of our labor and realize that we too can do this.  We too can establish additional streams of income so that we can rely less on the expected paycheck.

When we start realizing that there is money to be made outside work doing something we enjoy doing, we tend to focus more energy on it and as a result experience even better results.  Our confidence at work increases, we know we have something to fall back to, and whether or not we enjoy what we do for a living, we now have something else to look forward to as well, except now something we really enjoy doing!

As a result, we start undergoing some level of transformation. Our life outside of just the side gig starts to improve in many ways.  Our mere presence starts to exude confidence. We start talking to and behaving with higher ups as if they were colleagues not nearly as afraid as we used to be.

We walk with heads held higher and our chest spread wider not nearly as afraid about stepping on someone else’s toes.  We start realizing we have full control over our financial destiny. We start to realize that we can overtake the other Rats in the rat race.  We become fearless. Ok enough before we get carried away 🙂

This was a long winded way of conveying that working on a side business outside of work will boost your confidence at work because of the several factors discussed above and many more that are not.

Am I hallucinating or does this make sense? Do you feel the same? Do you disagree? Why? What has been your experience like?  Any stories you can share with our readers?

Here are additional thoughts on how a side business can boost confidence at work or otherwise.

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11 Responses to “Owning a Side Business Will Boost Your Office Confidence at Work”

  1. krantcents says:

    When I worked i corporate America, I had a significant side business. I was building up my income property (apartments & Shopping center). Not only did it give me confidence, it added to my financial reputation. I was CFO at the time. My colleagues admired what I was doing too. The other side of this is your boss may feel you do not need a job.

    • Sunil says:

      the flip side is always there, but if one is good at what they do, and hence the company (job) needs them more than they need the company, then the individual is even more so “empowered”

  2. Nigel Chua says:


    I agree with this – you’ve brought up something similar before, and I think that it’s a multi-factorial positive factor if/when one has a side gig that is profitable and valuable to others, outside of one’s own full/part time job.

    Why is that so?

    A few reason:
    1) Perception of competence – one’s perception of confidence is boosted significantly. No longer shall the yearly or bi-annual appraisal give you the shakes, as you know your value
    2) Actual competence – learning to handle a side gig or a full work at another site builds competences that has a carry-over effect (e.g. multi-tasking, delegating, work delivery, negotiation etc)
    3) Diversified portfolio – protects against potential loss of income, and this provides a LOT OF PEACE

    And this is just the beginning of an upward mobility and spiral e.g. bosses notice your increased competence, you become more vocal, you do better, and they promote you to do better and you do better etc. This is assuming one’s psysche, motivation and internal locus of control is benefiting from the stress from managing two or more jobs/income streams, as some people can’t take it and they crumble. Also note that there is often a learning curve where stress is the highest before the fruits appear, and this can double as a damage point if the stress from the part time gig affects one’s full time job.

    Nonetheless, being an employer myself, I don’t mind having employees who runs their own business, AS LONG AS WHEN THEY RUN MY BUSINESS, THEY RUN MY BUSINESS. I’d be pissed if when they run my business and they start answering calls or emails for THEIR business, when I’m paying them for their expertise on their time.

  3. Gabriella says:

    I am not going to lie but this is very true! Sometimes doing something on the side and having success with it means that you have more confidence within yourself too which shines out in all aspects i your life and one can then see a performance boost!

    • Sunil says:

      Welcome to the blog Gabriella. I am guessing you have first hand experience with this. Would love to hear more about it? I love the Stepford Wife Gravatar!

  4. Geoff says:

    Sunil, first off I agree completely….$100 bucks earned on your own from your blog or side gig gives you so much more satisifaction!

    Also, I strongly believe that not only do you get more confidence in the workplace from side gigs, but you can actually learn a lot more and bring some of those skills back with you. Take blogging for example, you can learn a lot about social media, SEO, and advertising tactics….all of these are valuable skills in many industries.

    p.s. I say go to Southeast Asia….it’s so off the beaten path I bet there are a ton of cool things to discover.

    • Sunil says:

      Welcome to the blog Sir. You make some great points.

      I’m a big fan of SEA. I was born in the Philippines! I have visited 7 of the 11 countries that make up SEA and I completely agree with you! There are 4 more to “discover”

  5. Wow This ia good thing to do. I never thought that having a side business will be of such great help and can do wonders in my personal as well as office life. I was thinking about stating a new business side by side but few friends suggested me not to because i won’t be able to handle both. But now after coming to the post i am thinking of starting the business again. Thanks.

    • Sunil says:

      Welcome to my blog Jason. You will find a lot more nay-sayers than the “yes men”. Only you can truly assess whether you can “handle both”. Just look around you, so many are doing it. What makes you think you can’t? Go for it man!

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