“The key thing to remember when making the switch from career employee to post-retirement entrepreneur? “You can’t do it alone. Find connections who understand and have the same problems, fears, challenges, and even joys you are going to experience as a new, older entrepreneur.” Wendy Mayhew, Seniorpreneur Expert and author of ‘WISER: The Definitive Guide to Starting a Business After the Age of 50’

Are you looking to pivot from employee to entrepreneur now that you’re retired? We’ve got a series of do’s and don’ts you don’t want to miss out on to make that pivot as graceful as a pirouette!

It’s been a long haul. Your working life. Your career. And now retirement is here. Ready for you, even if you aren’t ready for it. Regardless of how primed you feel, or don’t feel, most of us have been working, more often than not for somebody else, for 40+ years, which means most of us will admit that it has been a long haul. So, whether you are being forced into retirement due to unforeseen circumstances – COVID, financial issues, downsizing, etc., whether you are sad to be leaving your raison d’être behind you, or whether you are giddy with the prospect of finally retiring and have been planning this moment for some time, chances are you are ready for a break. A midday nap here, a mid-morning hike there, a mid-afternoon cocktail everywhere! But after the novelty wears off, and any one or all of the following kick in – boredom / a sense of needing something more / an urge to be busy with some practical, gainful use of your time / financial necessity – most retirees we know are ready to tackle something new. Something new that frequently involves a switch from employee to entrepreneur. Staff member to self-employed. Bullpen to business owner.

Make no mistake, this is a switch that can be terrifying, but thrilling all in the same breath. But fear not: you do not have to navigate the journey alone, and indeed, it’s not advisable to try to tackle any of this without help. We are here to help you make the pivot from employee to post-retirement seniorpreneur with the definitive list of do’s and don’ts to ensure a smooth transition.


Do… The Mental Prep Work

The best news of all when starting a business later on in life is that you have years of knowledge, experience and wisdom to back you up and to guide you. Which makes you more than ready to tackle the first ‘Do’ on our list: do as much mental preparation as possible before you dive into the practical nitty gritty of starting your own business.

What do we mean by mental prep work? Well, you need to mentally prepare yourself for the difference between worker and owner. It involves a different mindset: you have to think differently, act differently, and be prepared to navigate challenges and changes no matter what they are or when they spring up.

Thinking like a business owner means that the buck, the final management decisions, stop with you. You set the goals, you build the bridge to reach those goals, you do the work to get across that bridge and reach your destination. While this can be daunting, there is more good news: being the owner, the brains behind the business, means that you have the ability to say no if you think a suggested path is leading you over the railings and into the water. That’s not to say you’re always going to be right, but you are the one with the overarching vision and power of decision.

To help you cross the bridge without falling over and into deep water, it’s also worth fine tuning your knowledge, experience and wisdom with some superior brain work! Educate yourself on every aspect of business ownership and entrepreneurship: read books like WISER: The Definitive Guide to Starting a Business After the Age of 50; turn your car into a moving university and listen to audiobooks and podcasts on all things owning and running a business. Finances, hiring, firing, leadership, business planning, HR, client and customer service, office management… all this and more may be a part of your new life as a business owner. Make sure you have the knowledge to deal with every single aspect of owning a business.


Don’t… Think Working for Yourself is Going to Be Easy

Yes, you may have had some nightmare bosses in your time. But trust us: working for yourself is not going to be a stately walk through the retirement village park! As your own harshest critic, you are going to be harder on yourself than any boss ever was, and rightly so if you want to make a success of this.

For your post-retirement self-owned business venture to be a viable money-maker down the road, you’re going to have to raise your standards and put some benchmarks in place to ensure you’re meeting those standards and your expectations and goals. What’s more, while in theory you can set your own work hours, days, weeks and monthly schedule, in reality you can expect to work longer and harder than you’ve ever worked before. As owner, there is no set work schedule where once you leave the office you can forget about what lies on your desk until the next day. You will find that you need to focus on every aspect of the business, no matter how small or big, all day, every day.

The reward, though, is more than worth the effort.


Do… Expect to Start on the Bottom Rung

As an entrepreneur, you can expect to do every single job required to run your business yourself. Even if you do mean to have employees, there’s no better way to run a business than to know how to do every single task yourself. This means you need to diversify your knowledge of business in every possible way. The best way to do this? Start on the bottom rung as tea maker, toilet cleaner, then keep moving up the ladder as you tackle post office runner, sales rep, human resources manager, VP and CEO… you get the picture.

As an employee, you did one job: your job. This meant that while you became an expert in say, customer service, you could depend on others to handle sales, shipping, reporting, operations, marketing or accounting, for example. Start-up entrepreneurs, however, must be all things to everyone: top brass to brass knob cleaner, corner office management to office cleaner and custodian.

By expanding your knowledge base, and giving yourself practical hands on experience of every task, even when you are in a financial position to hire others to do your bidding, you will be perfectly placed to make a success of every aspect of your business. (On that note, here’s a bonus Don’t: Don’t treat your employees as servants placed in your orbit to do your bidding. Yes, you have done their job and know what you want, but Do allow them to shine!)


Don’t… Ignore the Financial Side of Things

The importance of this cannot be stressed enough. While you do need to have faith in yourself, your big idea, and your ability to make a success of your startup, that faith should not be blind.

Before leaping into the world of small business owner, make sure you have spoken to a financial adviser and have an accountant on standby to help you navigate the grind of daily and monthly financial admin, as well as big picture overall financials.

Do you understand the difference between revenue and cash flow? Do the words profit and loss statement and balance sheet make you shudder? Best you shake that shudder off and get used to having grown up conversations about money. (We know plenty of grownups who stick their heads in the sand about money. True story.) Owning a business is not just about being the boss; it’s about understanding how to create an entity that consistently generates revenues and profits with costs kept at the lowest possible level, and with perfectly kept books to keep you on the right side of death by taxes.

With regards to finances, you also need to do the following:

  1. Do bank at least six months of living and personal expenses to help you through what are all but guaranteed to be a few lean months at the beginning. It should come as no surprise that it can take months, if not a year or two, for a new company to gain traction and start generating revenues.
  2. Do develop a Lean Model Canvas, a one-page business model which allows you to set out reasonable expectations and profitability projections for the first year. You can download free Lean Canvas templates online (just Google ‘Lean Model Canvas Template’). This template is also included in Wiser, available here.
  3. Do cut your personal expenses significantly in order to have less demand on your savings and on your business in the early stages of operation, so that you don’t find yourself having to remove significant amounts of money from your capital on a monthly basis.
  4. Do remember that you won’t get paid in the beginning for all the extra hours you’re putting in. But if you’re patient and practical, and are working with solid financial advice, the financial reward will, in the end, more than make up for any upfront personal sacrifice.

Do… Make a Plan… and Stick to It

As your own boss you will find that procrastination may be your worst enemy. Do make a set schedule for each day, each week, and each month. Then stick to it. Of course, you will have to adapt your schedule during the course of each day as new tasks and challenges crop up, but the overall picture should tell a story of a day, week, month spent productively.

By creating such schedules, with “miscellaneous” time built in for unforeseen extras, you will be able to focus on both day-to-day activities and the bigger picture. Speaking of which, do include time in your monthly schedule to develop a longer-term business strategy with an aim of reaching profitability sooner. Don’t let the daily grind grind your big picture belief in your success out of the picture altogether.

Bonus Do… Take a Leap of Faith

Pivoting from employee to entrepreneur, especially later on in life, may be a leap of faith, but think of it as a leap of faith in yourself and your ability to achieve success. Besides, if you don’t try, you’ll never know.