6 Reasons An Entrepreneur Should Get A Job

This has been a very interesting topic for me as of late because of the mindset’s revolving around this topic. Reading online comments and hearing people talk about it on the streets, there seems to be 2 distinct thought processes here. Some people think that when an entrepreneur has gotten a job, they are a failure at running their own business. Similarly, some entrepreneurs feel like if they go back in a 9-5, that it feels like they have failed at entrepreneurship. They are hesitant to go and visit Caribbeanjobs or Jobstt and see what is available.

The other side of the argument is those that go back into a 9-5 because they have a strategy in mind that will ultimately help grow their business. I thought this would be a great topic to jump into and give my own thoughts as well. So let’s talk about it…when should an entrepreneur get a job?

As I sit back and sip on my tea (Infusio’s Chamomile, Honey & Vanilla to be exact), and I think about this topic, it really is a mindset issue. I mean there are quite a few reasons why an entrepreneur should get a job but that doesn’t mean you are a failure. Thinking that you have failed or are a failure is definitely something that can hurt you moving forward and you might start spewing that poison unto other budding entrepreneurs. So here are my top 5 reasons you should get a job.

  • Entrepreneurship isn’t for you
  • You need a cash injection
  • You need to learn more about an industry
  • You want to experiment
  • You have built an online business
  • You have received a great offer

Entrepreneurship Isn’t For You

So let’s address this really quickly. You decided to jump into the freefall of going into business for yourself and you realized after going at for a while, entrepreneurship just isn’t for you. This happens, at least you tried it and got the first-hand experience. I do believe however that everybody can work for themselves, given the fact that we are in the digital age.

I just don’t think everybody has a figured out the best idea to double down on or found the right process that could make being self-employed work for them. Or maybe you really believe in your heart and soul that you aren’t cut out for the roller coaster ride. Given the global economy and the revolutions happening with technology and systems, a 9-5 is no longer as secure as it was 20 years ago. So we need to re-shape our views and understand that being in a 9-5 is a roller coaster as well. Don’t be afraid to jump back into entrepreneurship with an idea that’s better aligned to you.

You Need A Cash Injection

Hey, it’s hard out here lol. Getting capital isn’t as easy as the banks or any financial institution makes it seem. I sat through a whole presentation from Nedco (National Entrepreneurship Development Company) and they spoke about how amazing they are and all the wonderful things they do for entrepreneurs without ever mentioning all of the collateral they require to work with them.

You can’t always get what you want from a financial institution, especially when they cannot wrap their minds around your business. Jumping back into a 9-5 may be your best bet. The key is in your mindset! If you view your 9-5 as your investor into your business, you approach the job with a completely different attitude. The other important caveat is to find a job that pays the most, that requires the least effort so that you can continue to give your business it’s required time and attention.

You Need To Learn More About An Industry

If you are dead set on building within a specific industry, then taking a job in your industry will provide you with the experience you need to help grow your business. While there is a lot you can learn from the outside, working with an established company in your space will give you some invaluable insights and also expose you to aspects of the niche you may not have been able to access on your own.

You Want To Experiment

As an entrepreneur, you know how hard you need to watch your spending. You also know it can get very hard to start to experiment on your business and not be able to recoup those funds in a timely manner. Getting a job will definitely give you a steady flow of income that will give you the safety net you need to start trying out new things in your business.

Just make sure you are taking notes of what’s working and what’s not, so you know where to start funnelling more cash into.

You Have Built An Online Business

I know you are probably reading this title and thinking if you have built an online business, why jump into a 9-5? Well, if the online business is running on automatic or semi-automatic. You should have location & time freedom. This gives you the opportunity to add another revenue stream or take a job in a space that gives you some fulfilment or in your niche so that you can continue to learn and gain experience.

When you know you are not relying on 1 income, you can approach a 9-5 with such a different mindset. Just ensure that the new job doesn’t take away from the quality of your online business.

You Have Received A Great Offer

As an entrepreneur, you need to create a product or service, you need to put yourself out there online and network offline. During the course of building your business, you have the potential to for a company to acquire your business or a company may reach out and offer you something great to join their organization.

All of these are great scenarios because they validate your business/product and it also validates you. People are taking notice of what you are doing and know how much you can add to their organization. All offers should definitely be taken into consideration and if you do decide to take it, you can always jump back out on your own whenever you are ready. If you have built an online business, you can potentially do both and enjoy a variety of benefits.

You only fail when you stop trying and it is very hard to get away from the entrepreneurial bug when you have been bitten by it.

During my time in building Droid Island and now KeronRose.com, I have received my share of offers. Either for collaborations or to join different organizations. I have done a few collabs and I am very choosy about them because you can’t always align your brand with any and everyone, also the opportunities have to work and align with what I am doing.

I have turned down a few job offers and I have 1 on the table right now that I am 95% sure I may take and for a few good reasons. The role is within my area of expertise, it’s in my niche, I have wanted to work with the organization, since I have only been in T&T for 5 years this will be another opportunity to learn, I can still run my online businesses because I have all the systems in place and finally, the money is very good lol. Oh yea, its also close to home.

Putting all of these factors into perspective, it hits all the right boxes for me to want to get involved in an organization. I have also wanted to start doing some online courses which may take away from my time to produce content, so having another steady flow of income while I start my online courses is going to be great.

I know Entrepreneurship is the way forward to various forms of freedom and it’s not something I will ever move away from. The courses I am going to be taking will help me become better at building digital businesses, become a better entrepreneur and dare I say, coaching may be something I do in the future…hmm. Interesting times ahead! I will probably reveal during the week If I have decided to go with the job and how my life will look.

This will be an interesting case study because then I can start talking to people about working a full 40 hrs and still building an online business so that we have multiple sources of revenue. It’s 2019, we ain’t making the excuse of not having time because of work, to build our empires.

So let me know in the comments below, would you guys & gals like me to document the journey of working a full-time job and balancing my businesses on the side? I think we can definitely grow together and some good conversations can follow. Let me know.


  1. Jo Dene July 6, 2019at6:54 pm

    Thank you for sharing.

  2. Jamila July 6, 2019at8:54 pm

    I would definitely like your feedback on balancing both an online business and a 9-5.

  3. Nancy Pierre-Campo July 7, 2019at12:41 am

    Absolutely. I would love to read about it.

  4. John Outridge July 7, 2019at4:42 pm

    This is a great article and very pragmatic, I can definitely relate to the examples you put forward, everyone thinks because you classify yourself as an entrepreneur it means that you must have a level of success attached to it, but the truth is most people when they become entrepreneurs is really to see what value they can create within that same 9 to 5 paradigm but rather create value for someone else , create it for themselves. I have started and sold many businesses and have quite frankly right now and completely run out of ideas for my next venture. I have decided to do some consulting in a new field to get a vantage point on an industry to see if may foster any new ideas. Am I not an entrepreneur still? Yes , because as long as you keep thinking about ways to add value, you will always be an entrepreneur !!! Great article keep it up !

  5. Lael Samuel July 10, 2019at1:54 pm

    I am really grateful for this! At this point in my life, that 9-5 is a reality that I have been taking a hard look at. Thing is: I thought that I would/am a failure for even looking at that option as an entrepreneur! After reading your article, boy was I wrong!

    Oh and yes, documentation of this part of your journey will be appreciated thank you.

  6. Beverley James July 11, 2019at3:42 pm

    I enjoyed reading your article very much and the points that you made are so true.I have had my own business for over 30 years and got physically and mentally tired and I knew I needed a change.I started opening up my mind first to going back to work, because when I was younger I left the 8-4 job to start my own business.Then the opportunity came and I jumped at it and I am still employed. There are days when I miss the freedom of setting my own schedule and activities and especially my power naps at 2.00pm when the energy wanes (which really do work by the way ).But this job has afforded me new experiences and has given me the break that I needed and the income to invest into new businesses online. I am now in the process of revitalizing my business again and getting ready for when I retire.Once an entrepreneur you are always an entrepreneur for I keep seeing ways of how to create cash flow. So yes please write about your journey—I look forward to it.

  7. rooms in anaheim April 2, 2020at11:12 am

    Its like you read my mind! You seem to know so much about this, like you wrote the book in it
    or something. I think that you could do with a few pics
    to drive the message home a little bit, but instead of that, this is fantastic blog.
    A great read. I will certainly be back.


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