When Should You Quit Being An Entrepreneur?

Can you quit being an entrepreneur? I’ve thought long and hard about this in the past few months.

It’s been sparked by some fascinating conversations with fellow entrepreneurs and reading Peter Shallard’s Why you should quit your business and get a real job.

I’m not announcing I’m quitting, far from it, but I do want to tell you I’ve thought about it more than once, in the past two years of having my online business.

When you’re in a 9-5 job and just not enjoying it, it’s totally natural to want to strike out on your own and start a business.

You discuss this with a lot of people as a way to make it through each day, and get you primed up to take action to eventually quit, and follow your dreams.

But as an entrepreneur, it is almost taboo to state `I’m thinking about quitting my business.’

How often do you hear anyone say `I’m thinking about walking away from it and going back to work in a day job.’

You’re meant to be in it for the long run right?

Having your own company is something others only dream of, so how could you possibly think about quitting?

Well I’m here to say you CAN quit.

It’s perfectly natural. Running a business is damn hard. If it was easy, then everyone would be doing it.

Being an entrepreneur is one of the most challenging endeavours

To all those people who make it sound easy, or disagree with my opinion, then I reckon you’re either lying or you’ve been incredibly lucky.

If we want to take one of the most obvious success stories, just look at the life story of Steve Jobs.

Apple was started in 1976 and it took decades of hard work and heartache before they became wildly profitable and the `Apple’ of almost everyone’s eye.

Steve Job worked himself to death and was notorious for being one of the most focused people on one singular vision.

No discredit to Steve and his empire (and I’m now a fully converted Apple fan), but that’s not my idea of having a life and a business you love.

It is ok to fail

This fantastic video, An Invocation for Beginning, is a must watch and makes so many great points on why we start anything meaningful, how scary that is and that you’re probably going to fuck it up.

What I particularly like, is when he says:

Even if you fail, the people who matter most in your life will still love you regardless.

If you say you’re closing your business, they will support you 100%. I think we often forget about that.

We place all this pressure on ourselves to succeed, and forget that regardless of whether we do or don’t, we’re still loved, no matter what.


You deserve to get paid what you’re worth

What so many people don’t realise is that entrepreneurs often put up with shitty pay, for super long hours, for much longer than they care to admit.

I am certain this is not good business. You need to charge what you’re worth.

You need to consider the time you are putting in, every waking hour, to ensure your business succeeds.

If you take a moment to work out your hourly rate, you may find you are being a complete fool.

Take into account client prep time, admin, endless hours working on tasks that you should outsource, and see if it’s adding up to decent earnings.

Then add in the amount you invest in infrastructure to run your business – software, tools, services, office space, security, team members.

Take your total profit and subtract the total of these operational costs and then divide this final amount by the amount of hours you’re REALLY working.

If it’s looking like a minimum wage job, then perhaps you should reconsider and go back to the job market.

Don’t forget the opportunity cost of a real job

I talk to many people reminiscing about their past cushy jobs.

You start remembering all those great benefits you got as an employee like free medical care (North Americans in particular are obsessed with this), employment insurance and pensions (retirement plans).

Don’t you dare forget about paid holidays, business travel on the company (while you rack up the frequent flyer miles), being able to use the company account to woo clients, having your expenses reimbursed and the opportunities for employee training and development.

I’ll admit it, sometimes a well paid job is an attractive alternative.

You don’t have to do everything yourself

I don’t condone people who try to do everything their selves in a business.

Well at least not after year 1 or 2, when you really should know better, and you recognise that investing in others will ultimately help your business to grow faster and be more profitable.

I do, however, wish to sometimes not be the chief decision maker.

Even as a head of department, in my last ever job I had back in 2008, I still enjoyed bouncing ideas off my manager and having him make the final decision on a project or initiative.

The fact that I still got paid for working, whether the project succeeded or not, was a big bonus.

 Your job and your business should be enjoyable

Richard Branson is famous for saying he would never run a business if it wasn’t a ton of fun.

Richard Branson On Having Fun In Business

While I’m yet to make billions and have a ball of the time, all the time like Richard, I do inject fun into my business wherever possible.

The minute I feel like it could be a bit of a drag, too much hard work, or it’s sapping my energy, I get up and shake my booty.

Then I reprimand myself for working too hard, not disconnecting, and focusing on the work that doesn’t matter.

If you’re not loving what you’re doing AND you’re not making money, then you should be looking for a job!

What do you think? Are you better off quitting your business and getting a job? Have your say in the comments below.

  • http://www.facebook.com/susan.hand3 Susan Hand

    I don’t think of it as quitting, it’s more like evolving. Life changes, we make different decisions and I really think it’s much better than when I first started “working”. Back then you were making a decision for life. Now you have different opportunities and can make choices along the way. I’m not sure that I’ve stopped evolving, but I know I have more fun now making money and I’m here to say that Branson’s right.

    Thanks for this thought provoking post!

  • http://suitcaseentrepreneur.com/ Natalie Sisson

    Great point Susan. It certainly could be referred to as evolving. From career, to business and then putting it back into a career. Who knows the second time around you may be a far more effective employee and teach the business owners a thing or two as well. Branson is right – the man owns an island and goes out paddleboarding each morning – how could he be wrong! :)

  • http://alifeonyourterms.com/ Liz Seda

    Hey Natalie,

    What an interesting post. You’re right. Quitting your business just seems unthinkable! But that’s just for me. I would much rather work the long hours that I do now for barely enough money to get by (which will change after the retreat of course), than work a single minute for someone else.

    The anxiety of having to be under the thumb of someone else trumps the amount of work I have to do every day. So for me it is unthinkable.

    For others, it might be better. Maybe they really don’t want the responsibility of running a business and not ALWAYS knowing exactly how much money they will get. Maybe they are more comfortable being lead than leading. In which case quitting their business may not be such a bad idea at all.

    It’s interesting that we’ve married the idea of entrepreneurship and happiness. I have done this as well. Most of us can’t ever be happy working for someone else. We are passionate about what we do. However, people who work at corporate that don’t want to be entrepreneurs aren’t always passionate what they do so they don’t run around screaming about getting a corporate job to be happy like we do about creating businesses.

    That’s all I got to say bout that.


  • Peter Sterlacci

    Ah the eternal question that any solopreneur / entrepreneur faces on a periodic basis. I think it is a normal question to ponder for sure. I know I do. I fear not being able to provide for my family and the thought of a steady paycheck creeps back in. I then remember how miserable I was in my 9-5 gig, but then I remember how I did not have to worry about my bills, and then I think how much I love what i do as my own boss, and then…. You get the picture!!! Never ending cycle! But I do agree Natalie that it is OK to walk away as sometimes life changes and we don’t really have a choice. Today I choice to keep at my business! Tomorrow??
    Thanks for a great post.

  • Rose

    You can quit your business and go back to being an employee but I don’t think you can actually quit being an entrepreneur as it takes a certain personality and mindset to become an entrepreneur and this doesn’t go away just because you have chosen paid employment.

    I have been lucky enough to enjoy the best of both worlds over the past few years (employed 20 hours a week and the rest of the week entrepreneur), so can see benefits and downside of both. However, I don’t think I could ever stop my brain ticking over with new business ideas regardless of employment status.

  • http://suitcaseentrepreneur.com/ Natalie Sisson

    Yeah I love this Rose and I think you’re absolutely right. So long as that entrepreneurial thinking and mindset is funneled towards the best use in terms of projects – both in business or a career. Sounds like you’ve made great use of having the best of both worlds.

  • http://suitcaseentrepreneur.com/ Natalie Sisson

    Hey Peter. It is a question that comes up more often than we think, but I’m not sure we voice it out loud. We tend to act in isolation and try to push through the fear or just get over it.

    I think having an open forum to discuss the feelings would be beneficial (without getting woo woo or becoming a shrinks office) – but to judge whether people are genuinely unhappy and correct in their assumption that they’re better off working for others than themselves, or whether they’re just facing fear.

    New business perhaps? The entrepreneurs shrink – oh we have Peter Shallard for that :)

  • http://suitcaseentrepreneur.com/ Natalie Sisson

    It does seem unthinkable in the early stages for sure, but I’m certain there are people who have been in biz for themselves and just scraping through for 5 or 10 plus years, and that’s just draining. For them I think it’s potentially easier to accept that they gave it a great innings and now they need to move on. On the other hand it might be even harder as it’s all you’ve known. I do admire people who absolutely love their jobs! But you’re right I love working for me – and all my clients :)

  • Susan Andrewes

    Hi Natalie. I think you have touched on a really, really important point. I am actually going to be one of those to disagree with you and say that running your business doesn’t have to be difficult! We make it difficult because we are constantly told that we have to work incredibly hard even to just make ends meet. We’re told that running your own business is more about the passion than the money.

    Where people fundamentally go wrong (whether you are in a 9-5 job or an entrepreneur) is that they believe that their success, happiness and fulfillment depend on a certain outcome (i.e. I will be happy when I make £50,000/£100,000/name your figure; I will be successful when I have a certain number of clients etc; once I earn X, I will finally have the freedom and time to do what I really want with my day…). This is the ‘Achievement leads to Happiness/Success’ etc model. The problem with this outside-in model of success is that is that we are constantly striving for something and never quite making it; or we reach the income/outcome we thought we wanted, only to find that that doesn’t bring us real happiness either.

    When we realise that this model is a fundamental myth, and that, in reality, ‘Happiness leads to Incredible Success/Extraordinary Achievement’, we begin to look at our lives and businesses in a whole new light. When we realise that nothing outside of ourselves can ever bring us happiness or success, the only thing left to ask is ‘What would be fun?’ If you have no attachment to a certain outcome in order to feel successful/happy/worthy as a person, it is amazing what kind of results (financial and otherwise) you can achieve!

    Would love to hear your thoughts :-)

  • Angela

    Nice one Natalie…it’s very necessary to talk about the old elephant in the room sometimes. If you’re not feeling the love you shouldn’t be doing it right. 😉

  • http://twitter.com/KrystinaFeucht Krystina Feucht

    Great post Natalie!

    I agree with the litmus of enjoying what you are doing and making money doing it. And I love Susan’s comment about life changing. I’ve seen business owners that sell their business and retain an executive position in it. They came to the point where that type of arrangement worked best for them.

    I think it comes down to constantly asking yourself and being aware of how you feel about the work you are doing and does it serve the purposes you need for you (and possibly your family).

  • http://suitcaseentrepreneur.com/ Natalie Sisson

    Yes definitely agree.

  • http://twitter.com/kpdurand Kyle Durand

    This is a great post, Natalie! One of the dirty little secrets that most entrepreneurs will not readily admit is that almost all of us have looked to our peers in “regular jobs” with envy at some point. The grass certainly appears greener on the other side when we are laying in bed with our eyes wide open at 3am figuring out ways to make the next payroll or what in the world it will take to get someone to finally sign up for our program, and our employed counterparts are sleeping cozily in their beds knowing that the paychecks will just keep coming in as long as they get out of bed and show up to work. The apparent glow wears off quickly when an entrepreneur takes a broader look at what those people give up, though. Many of the freedoms we enjoy on a daily basis are simply just not options for our employed peers – especially working when, where and on what we want. To me, those freedoms are priceless and irreplaceable by a paycheck. Like a ship at sea, we all have our ups and downs on our entrepreneurial voyage. In my opinion, the key to success is maintaining perspective by keeping our eyes on the horizon. Thanks for the reminder!

  • http://suitcaseentrepreneur.com/ Natalie Sisson

    So true Kyle. It’s all about getting perspective. We can choose what we do on a daily basis (more than we know) and that’s a luxury so many in 9-5 cannot afford or easily attain.

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  • http://www.loveyoursmallbusiness.com Janine Ogg

    Great post!

    I love Susan H’s comment about viewing your decision to leave a business as ‘evolving’ rather than ‘quitting’. I also loved the reminder that whatever you decide to do, or no matter how massively you fail (or succeed) the people who love you most…..will still love you! This is easy to forget and so many of us fall into the trap of getting our sense of self-worth or self-esteem from what we ‘do’ rather than who we ‘are’.
    Thanks again for another ripping post Natalie.

  • Carl Spira

    I think anyone who starts to have these thoughts should read Dan Kennedy’s books. He is one of the best copywriters and direct mail marketers and has firm opinion on things based not upon an MBA or books read but personal experiance. He is as some of you would say “streetwise”. I have read many of his books and I find them absolutely invaluable. Be aware though that he is frank and does not write to please the teacher. I am presently reading “No B.S. Ruthless Management of people and profits” This is not hype, Mr. Kennedy charges around 18-20k a day for his services and you can only reach him via fax! You can find almost all his books on the Kindle(recommended). Mr. Kennedy does not own a mobile phone nor those he use email. If you want your life back without going back to a job, pick up his book. Might be the Bible you have been looking for!

  • http://suitcaseentrepreneur.com/ Natalie Sisson

    Wow are you his PR agent? If not you should be. Have definitely heard great things about him so I’ll go and check out his range of books thanks Carla

  • http://suitcaseentrepreneur.com/ Natalie Sisson

    Ripping – you make me laugh. Glad it’s ripping though and yes I think being loved regardless of your failures or successes is such a key thing to remember. People don’t just stop loving you cos you screwed up or didn’t make it. They love you more for giving it a shot in the first place.

  • http://twitter.com/ejdlee Erica Lee Garcia

    Hi Natalie! Timely post. One of my good friends, an inspiration/mentor who was an evangelical solopreneur who got ME hooked! – recently got a day job and she is super-happy. It wouldn’t surprise me if I became employed by someone else at some point. But it will be with some truly kickass employer (definition: won’t make me take out my nose piercing. That is my litmus test for awesomeness from here on in)!

    Your call for self-love in the face of ‘failure’ is well-taken; myself I don’t think of leaving a business to move onto something that works better for you as failing – it’s about reading the signs and having the courage (and I guess humility!) to make the change. Depends on the individual and even more so on the timing.

    Arguably staying in an entrepreneurial gig where your business isn’t thriving and you’re not enjoying yourself for years on end but you’re just too stubborn to consider anything else could be more aptly called failure. For others the freedom and flexibility is worth the price, so it’s a victory if they are able to keep their bills paid – an awesomely defiant gesture to stay free from the clutches of The Man – in which case who could argue that they aren’t the most successful of all?

    Thanks for the thought-provoking read!

  • Mary Anne

    Hi Natalie

    Good post. Though what do you think of being in the situation where you can’t get a full time job despite trying? This is not to say I’m “unemployed”. I have been struggling starting up my business as an architect, writer and musician. Even contract work hasn’t worked out so far – disillusioning for sure! And financially I’m slipping further down the rabbit hole…

    Mary Anne

  • http://suitcaseentrepreneur.com/ Natalie Sisson

    HI Mary Anne – it’s hard to say without knowing much about your background and what you are doing proactively and what you’re not doing to market yourself. It sounds like your business is pretty diverse and that may be the problem in itself you know. People may not understand what you do and how that helps them.

  • http://twitter.com/SharmeenAGangat SharmeenAkbaniGangat

    Excellent post! The dilemma is that whether we decide to be on our own or work for someone else, there is always this “what if” that pinches. So, it’s better to go with what the heart desires. In addition, the biggest risk in entrepreneurship comes from quitting itself because we may end up leaving when we are about to reach the goal post.

  • http://www.budoofbliss.com/ Marty

    I realized that I need to change what I do on the “business” front… And focus more on things I love. Focusing on my passions will make me more blissfull even if I don’t roll in the dough, not that Im against it. I will still do my thing and write about it.. I will probably focus On Niche sites, and focus less on monetizing my lifestyle blog… Lifestyle design is a tough Niche I think I can do better in another one, and still write about my journey and be happy. Great Post!

  • Shaun Kruger

    I quit my business 18 months ago. I got a day job and called it “rehab”. I hated my customers and was stagnating. It took almost a year to become really interested in technical projects again. Sometimes you get burned out and need to find a place where you can recover, learn, and recharge for your next attempt.

  • Cheval John

    This is an interesting article. I have to agree to a certain degree about if it is not fun anymore, then you should just close up shop. However, I really can’t imagine someone going back to the “real job” because of all the “benefits” and pay that comes along with it.

    It’s really given up control of your freedom if you want to fulfill your purpose in life.

  • Eteuati Auva’a

    Natalie, for the record my world, if not ‘The World’ is so much better just knowing you’re out there doing your thing in the world. Often the real fruit of our work is hidden from us, while we are striving, but you definitely touch many lives.

  • Joshua Axford

    Thanks Shaun, The only thing that gets me out of bet at every morning is obligation, I have lost the love. I feel trapped with the responsibility of Customers, Suppliers, Staff, Legal and Government obligations, etc… I a seriously contemplating “rehab”.

  • Jeshua Zapata

    I liked what you mentioned PROFIT & PASSION. In the event your not excited, or don’t have any passion for what you are doing, then why continue to do it? You have to look at the long term view and see if it still excites you. PROFIT, if its exciting but you are not getting paid to live a comfortable life, and continue to GROW you have a problem.

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