5. Plan Your Life After the Sale
Money matters and personal plans so you know what success looks like beyond the cheque
Problem Statement.
You spend years focused on revenue, staff dramas, GST, suppliers and customers. Then one day the deal money hits the account, the calendar clears, the phone goes oddly quiet. For a while it feels like a holiday. After that it can feel like a void.
Without a clear picture of life after the sale, owners can drift. Some burn through cash faster than they realise. Some jump into the next venture out of boredom rather than purpose. Some miss the structure and identity of being “the boss” then look back at the exit with mixed feelings despite a decent price.
What An Owner Might Say.
“I just want to get the deal done. I will think about life after once the dust settles.”
“As long as there is enough in the bank, everything else will sort itself out.”
“I am a bit scared of stopping. Work has been my hobby as well as my job.”
Why It Happens.
For many New Zealand owners the business is not just an asset. It is a role, a community and a story about who you are. Letting go of that can feel bigger than any spreadsheet. It is not surprising that people put off thinking about the personal side until very late.
The money piece can feel overwhelming. Tax, investment choices, new structures, possible advice fees. You know enough to realise mistakes could be painful although not enough to feel confident in a plan. It is tempting to park the whole topic and simply hope a good accountant and a quick term deposit will do the job.
Most owners have also never had so much choice. For decades you answered to customers, staff and deadlines. After a sale the constraint is gone. Total freedom sounds lovely in theory. In practice it can feel like standing in the middle of a field with no track to follow.
What To Do About It.
Treat “life after the sale” as a project, not a mystery. You do not need a perfect script. You do need a rough picture of what a good next chapter looks like for you and the people close to you.
Start with three simple questions.
• How do I want my time to look in an ordinary week two years after the sale.
• How much after tax income do I want that life to generate without stress.
• In what ways do I still want to contribute so that I feel useful.
Write honest answers, even if they feel provisional. That becomes your first sketch of success beyond the cheque.
Next, get curious about the money rather than scared of it. Work with an adviser who can model a few scenarios without trying to sell you a product at the first meeting. At a high level you want to know
• Roughly how much you will keep after tax and costs
• What level of spending that pool can support sensibly
• How different choices about homes, gifts, new ventures or debt payoff change that picture
You are looking for a range that feels sustainable, not a single magic number. The aim is to align lifestyle expectations with what the sale can realistically fund.
Think about structure as well as size. Many owners feel calmer when their post sale capital is divided mentally into buckets. For example
• Safety bucket for mortgage reduction, basic living costs and rainy days
• Long term investment bucket for retirement and future income
• Fun and family bucket for travel, house tweaks or generous gestures
You may end up using different names. The point is that not every dollar is equally available for the next shiny idea.
Then sketch the non financial side. List the roles you already play or would like to explore. Mentor, investor in other SMEs, trustee, volunteer, part time board member, learner, traveller, grandparent on call. Note which ones give you energy rather than just status. In my view at least one future role should stretch your brain a little, one should connect you with people and one should simply feel like joy.
Test a few of these before you sell if you can. Join a board, take a short governance or writing course, increase a hobby day by half a step. You are not trying to create a second job. You are giving your future self proof that satisfaction exists outside your current office.
How To Keep The Momentum.
Once you have a first cut plan, talk about it with the people who will live with the consequences. Partners, whānau, sometimes key staff. Check that your picture of the next chapter roughly aligns with theirs. It is better to discover early that your partner was expecting more shared time while you were quietly planning another full commercial schedule.
Set a simple review rhythm. Every six months during exit preparation, glance at your notes and ask three questions. Has anything changed in my life that shifts timing. Has anything changed in the business that shifts what is realistic. Have my own priorities evolved. Adjust gently rather than throwing the plan out.
After the sale, treat the first twelve months as a transition season rather than your new normal. Allow more rest than you think you will need. Say yes to a few interesting opportunities yet protect time for decompression. Delay any massive fresh commitments until you have lived at least one full year without end of month payroll on your mind.
Watch for the urge to rush into another big venture purely because empty space feels uncomfortable. If you genuinely see a great opportunity that fits your life and risk appetite, excellent. If you are mainly trying to recreate the buzz of being needed, pause. Talk it through with someone who will tell you the truth, not just what you want to hear.
Golden Nugget.
“A successful exit is not just the day you bank the cheque, it is the life you are still happy with five years later.”
How RegenerationHQ can help.
RegenerationHQ works with owners who want the sale of their business to serve their wider life, not the other way round. In my view that means planning your next chapter in parallel with preparing the business, rather than as a late night afterthought once the agreement is already with the lawyers.
Support can include structured conversations about your life goals, simple frameworks for mapping time, money and contribution, plus help turning that thinking into clear guidance for your accountant, financial planner and legal team. RegenerationHQ does not replace those specialists. It helps you walk into their offices with a sharper sense of what success looks like, so their technical work actually fits your values.
Within a wider Exit Prep Programme, this life planning threads through decisions about timing, deal structure, handover and post sale involvement. The outcome is a business exit that feels like a step toward something chosen rather than an escape from something painful, which is a far better story to tell yourself when you look back on this season.
If you want a steady guide beside you while you get ready for one of the biggest decisions of your working life, RegenerationHQ is ready to help you walk that road with clarity and confidence.