A successful transition from a busy work role, either your own business or a salaried senior leadership position in a company, is not an easy exercise. It is usually a 3 – 5 year journey to leave your current position successfully. It then usually takes a year or two to adjust to the new life you have open to you.
The time to start thinking, planning and taking action is about 5 years before you fully exit your business.
Trent found that the transition was not easy
Trent is a business owner who had a couple of failed attempts to exit his business successfully. He told me it was much harder to exit his business than to start it in the first place. He had tried to pass the baton of ownership and leadership in his business to his son. However, his son was more technically oriented, and struggled to handle all the people management tasks of running the business on his own. They stopped that planned transition, regrouped, and came up with another plan. They eventually created a partnership between the son and another senior employee. With some legal advice, and guidance from the father who continued for 2 years as a Director, they learned to run the business successfully. It became almost a 10 year process before the father could fully exit.
Anton’s transition story.
Anton has been a very successful business owner for more than 30 years. His business has set him up well financially. He has been successful with growing his client base and team. And he had been a very community-minded person, a strong contributor to his local Business Chamber and other networking groups. Over the years he has built a good reputation and made a lot of friends and acquaintances. After working very hard for 20 years, during his 50’s he started to take some regular short overseas trips with clients and business associates each year to various parts of the world. They would usually combine a conference or a trade show, so he could write some of the expenses off on tax. These trips stirred something deeper and he realised he wanted to start enjoying more of the rewards for his years of hard work. He was now in his early 60’s and his wife had just been through some moderately serious health issues. He sensed a transition was happening and he wanted to get ahead of it.
He reached out to me to assist him to think about how he would manage his transition. After I listened to his story, I realised this was an important moment in Anton’s life. He was not the type of person who usually reached out for assistance. He was the one used to giving assistance to his clients. It was a privilege to sit with him and help him think about the journey ahead.
He could see a 3 – 5-year transition from busy fulltime work to selling some parts of his business. His whole identity and life purpose until now were entwined with his businesses. He was keen to retain a couple of advisory roles with key clients for a few years longer. This was not about money, but about an ongoing sense of purpose.
We divided up the next 10 years into a time frame for the next 5 years as he disengaged from his business, and then the next 5 years as he sold his business and began to enjoy a bigger life of purpose. We spent a few sessions talking through all the aspects of how this could happen.
We divided his activities into ‘work related’ and ‘non-work related.’ (See table below.) This helped him to realise he did not have many non-work-related activities in his life at the time. For more than 30 years, he had been very focused on his business, more than interests outside of work.
We talked through the kinds of things he might like to do if work did not take up all his time, focus and energy. He had a couple of activities he had always wanted to try and there were some things he knew his wife and he could enjoy together, including travel. They already had one granddaughter, with whom he was besotted. The goal was to find a few more activities he could start testing over the next couple of years.
In a similar way we looked at his work roles and found some things he could start to hand over to others on his team in the short term. This would allow him to focus on the business rather than being as busy working in the day-to-day business operations. There was some work to do in his business to prepare it for sale which he began to scope out.
This framework started the ball rolling. After 6 sessions over about 4 months, involving considerable thought and discussion with Anton, and he with his wife and family, he had some clear plans for how he could take the first steps to move towards his goal. He could see how it would be 3 or more years before his business was ready to sell. However, he was glad he had started to think about the larger purpose beyond work. A hard stop would not have suited Anton. Like most of us, he needed a transition.
A simple structure to assist you think and plan
| WORK RELATED | NON-WORK RELATED | |
| Short Term (1 – 2 years) | Assess readiness for sale of business –
Create clear plan to bring up to sale readiness over 2 years. Hand over key responsiobilities to team members. Work more ‘on the business’ than ‘in the business’. Cut back to 4 days per week
|
Discuss and create a joint wish list/ bucket list with partner
Work on health & fitness Complete house renovation Some extra travel Ensure finances are strong Find an activity/hobby or two to test |
| Medium Term (3 – 5 years) | Create a strategy for sale of business
Aim to sell by end of 3rd year – especially if need to stay working in business after sale for a smooth transition. Ensure a good financial result. Market his part-time consulting Work 3 days per week. |
Activate his financial/tax plan
Pursue a book writing idea Some family heritage searches Select new hobby/interest to pursue |
| Exit current Work role | ||
| Longer Term (5+ years – post current role) | Lock in consulting opportunities or Board positions – 2 days pw max | Pursue Bucket list items
Enjoy new hobby Enjoy travel
|
Other important things to consider
- Grief of losing your work status and relationships
Once you stop work, there is quite a lot of loss, including loss of status, relationships and identity. As part of this transition, you must be more purposeful about relationships. It is easy to mistake all your colleagues and work connections for friends, only to find that after you leave your important work role, that most of them do not call. Many men must rebuild relationship circles after finishing work. It is easy to accidentally become a loner. Golf clubs, church groups, and the like, are great places to find like-minded people to build new connections and friendships. - Identity issues – who are you if you are not working?
Ben Crowe in his book, Where the light gets in (2026), helpfully discusses how we can discover more deeply who we are when we face the vulnerable task of getting to know ourselves separate from what we do. Ben states that most of us are human doings rather than human beings. We introduce ourselves as John, Business Mentor, assuming that explains who we are. It does not. Retirement, or selling your business, forces you to confront who you are ‘without work’ defining you, whether you want to or not. Many struggle with this. This is definitely worth focus and effort as part of your personal journey during the transition period. - Structure
Somewhat surprisingly, after leaving a busy work role, it can be difficult to find a good daily routine. Very capable professionals may need to be reminded to create a daily plan. For years, their days have been filled with so many things without them trying. It can be very disorienting when all the structure of the workplace is not there, and you are not as busy.
Books on retirement (E.g. How to retire and not die by Gary Sirak; or, How to retire happy, wild and free, by Ernie Zelinski) talk about this need for structure. They suggest planning 3 things to do with your day each day. These 3 things might be as simple as doing some exercise, going out for a coffee with your partner, and then doing more on a garden project in the afternoon. Otherwise, it can be easy to lose structure and meander. - Part-time work
Stopping work completely is often not the best choice for men in retirement. Like Anton, taking on part-time consulting roles to clients in the industry in which you spent years working is a good option, all the while you have energy and mental acuity. This provides some of the structure, purpose, and social interaction that feeds the soul. There will be some income as well, which may be important to top up savings.
John Drury Business Mentor – mentoring to develop the leader within you, and to raise up and empower the leaders around you. If you would like to discuss how you can plan your transition to a life bigger than work, please reach out for a free conversation (Book here).
LIKED THIS? READ MORE
Here are a few of my favourites to help you integrate your work into all other parts of your life.