The “Catch-22s” of starting and running a business

In my consulting practice, I come across business owners at all stages of their business’ life. This week, I realised that starting and running a business is full of Catch-22 scenarios. For those not familiar with the term, a Catch-22 is a requirement that cannot be met until a prerequisite requirement is met, however, the prerequisite cannot be met until the original requirement is met.

It was made famous by the iconic book by Joseph Heller published in 1961, which was made into a movie starring Jack Nicholson in 1970. By definition, Catch-22s are unsolvable so where does that leave business owners? In this article, I discuss some of the Catch-22s new businesses typically face, and offer ways they can (at least attempt to) tackle them.

1. You can’t quit your day job so you have no time to launch your startup

When to quit your full-time day job is usually one of the first questions an entrepreneur has to answer for themselves. There’s no doubt that keeping your day job is sound from a financial perspective – keeping the cash coming in while you launch provides an easy way of financing your startup as you go or helps you build a buffer of savings for the lean times when you do quit your job and start relying solely on your business for income.

But this is not always the best idea and here is where the Catch-22 comes into play. How can you focus the right level of attention and time it takes to properly launch a startup when one of your feet is still in the door of another room. Depending on the workload and demands of your day job, not quitting could end up killing your startup before it even takes its first breath… and could kill your dream in the process.

How to tackle this Catch-22:

Realistically ask yourself if you can effectively manage a full-time day job and launch a startup at the same time. If the truthful answer is yes, then go for it. This is possible if your day job is not demanding and is relatively flexible on work hours and ability to take time off as needed. If the answer is no, my advice is to build yourself a savings buffer (or get some form of finance), quit your job and dedicate yourself solely to your startup.

For more advice on when to quit your job and go freelance, read this.

2. You’ve quit your day job to launch your startup but the work/income isn’t coming

Let’s say you went ahead and quit your day job and plunged yourself 100% into launching your startup, as I did. Well, this Catch-22 scenario is all about that scary period between launching and earning enough revenue to pay your bills. You’ve done you’re business plan, set up your business structure, define your products/services, worked out your processes, hired staff if applicable, set up your operation and maybe even done some sales and marketing. But inevitably there’s that lull period. If you’re lucky, this period is short but it very well may not be.

The Catch-22 here is that it took a lot of courage for you to plunge in but this lull-period threatens that very courage and can shake your confidence at its core. While you sit and wait, doubts settle in. Did I do the right thing? Should I have kept my day job a little longer? Is this even going to work? What if I never make enough money? Should I give up and go back?

How to tackle this Catch-22:

If you’ve done your planning and all your homework as listed above, trust it will happen. But make sure you really understand – and you can articulate out loud in 60 seconds – your value proposition. That means the features and benefits of your product/service, and what makes it different – and better – than that of your competition. That, and make sure you have a good sales and marketing plan.

Unless your product/service really has no value to anyone (which is hopefully not the case!), there is no reason you shouldn’t succeed if you have done the above things. If you are still struggling to make enough revenue, hire an expert to take a look at your business plan and sales and marketing plans and advise on improvements if necessary.

Read this for the 10 most important things to plan/research before launching your business.

3. You’re too busy working in the business to work on the business

This is becoming a cliché among business owners but it basically means this… When you’re crazy busy dealing with every tiny aspect of your day-to-day business operations, it’s impossible to pick yourself up out of that ditch and take a helicopter (strategic) view of what’s needed to grow your business. But of course, if you do take your head out of the ditch, the worms start crawling in and you’re immediately out of control again.

This is probably (other than cashflow issues) one of the biggest pain points for business owners. And this is why I have a job! But here’s the thing, when you neglect working on your business, you perpetuate the craziness… you neglect your staff, you grow tired and stressed and start neglecting your clients. It’s a sad story all round and a fast-track to burnout and business failure.

How to tackle this Catch-22:

Stop. Get out of the ditch! Make a list of everything you have to do. I mean everything. Then go through the list and circle or tick all those tasks that meet one of these four criteria:

  • Does it relate directly to a client project or order?
  • Does it relate directly to a prospect or qualified lead?
  • Does it relate to developing a new product or service?
  • Does it relate to your financial, legal or tax obligations?

For all the items not circled, delegate them to your assistant if you have one, outsource to a supplier or service provider, or just cross it off the list altogether. Then for the items circled, prioritise and get working!

For more advice on managing your time and workload, check out my blogs on 3 secrets to exceptional customer service and How to make (and keep) client promises.


Peer-Business-Consulting-Angeline-Zaghloul-5What did you think of this article? Post your comments and questions below. And if you found this useful, please share with your networks.

About the Author: Angeline Zaghloul is an expert in business strategy, client management and business processes, and is the Principal of Peer Business Consulting, a Sydney-based consultancy providing strategy and operations support to startups and small businesses.

* Portrait by Markus Jaaskelainen.

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