Starting Over Is the Wrong Frame for a Career Transition
Updated: 5 days ago
A successful chapter ends and the language gets sloppy fast. People call it starting over. The résumé is still there. The experience is still there. What moved is the structure that made it all make sense, and the title that told everyone else what to call you.
Lauragaye Jackson, a fractional CMO and executive coach, thinks that word is wrong. She spent years in senior global marketing roles across Canada, the United States, the Caribbean and Europe. Then eighteen months arrived that would have justified the word for most people. She built from the experience instead.
For a founder leaving a company, or an executive whose role is eliminated, the practical answer is the same. Take inventory before you reinvent. Learn to tell the story. Then move before the proof shows up, because the proof arrives after the decision, not before it.
Inspired by Paper Napkin Wisdom Episode 395 with Lauragaye Jackson.
Eighteen months that would have justified the word
Jackson's transition was not one clean decision.
Inside roughly eighteen months she went through the end of a thirty-plus year relationship, the death of her mother at ninety-six, the elimination of her executive role, the sale of the marital home, a son leaving for university, and a return to formal schooling. She referenced the Holmes and Rahe Stress Scale in our conversation. It measures 43 major life events. A score of 300 or above carries an 80% chance of a stress-induced health breakdown. Hers came to 364.
Some of it was anticipated. Her mother had been unwell for some time. The move to university was on the calendar. The end of the relationship was not, and neither was the job. As she put it, they kept compounding on each other.
What I notice is what she did with all of it. The easy reading is erasure. Everything familiar moved, so everything has to be rebuilt. She asked a different question. What from the previous chapter still belongs in the next one?
Her marketing career became part of the coaching practice. The years developing people became part of her value as a coach. International work shaped how she reads people across cultures. Even a network she had let go quiet came back into play.
Nothing useful had vanished. The packaging changed.
Take the inventory before you reinvent
Experienced leaders can get so focused on what disappeared that they never count what remains.
Jackson's words: "nothing that you've experienced is wasted. It's really what part do you want to carry forward." She walks clients through strengths, lived experience, values, relationships and interests before anyone talks about a title. And she is honest about why people skip it. "everyone just kind of wants to jump to, here's the job. I can make this amount, this is what it is. But is it aligned with your strengths, your values, your passion."
For a founder, the same principle holds. The company was one expression of your ability. It was never the full inventory.
There is a pressure point underneath this one. People in transition feel they have to make something happen, anything happen. I used to describe my own version of it as putting every iron in the fire at once, five hundred irons, until the iron smothered the fire. Too much iron on top, not enough fire underneath.
Jackson also made a point I did not expect from someone who calls herself a data geek. The emotional part of this is not a distraction. The low moments are data. They tell you what you fear and what you value. She also made room to grieve, because grief that is skipped shows up later and stops you moving.
The rough order she follows:
Strengths with real evidence behind them
Experiences that shaped how you see people and problems
Values, named specifically, not as a word on a wall
Relationships already sitting in your contacts
What gives you energy, and what reliably drains it
Nobody sees the new chapter until you tell them about it
Jackson had been known for years as a senior marketing executive at a large Canadian organization. Becoming a fractional CMO and executive coach meant other people had to learn a new story about her. That is more than a change to a LinkedIn headline.
She is a marketer, so she treated it as a rebrand on herself. What she now offers, why the previous experience matters, how the pieces connect. The same work shows up with her clients: look at the inventory, then shape how the story gets told so it lands with the person across the table.
Two things she is firm about. The story has to be told with confidence and conviction. And it has to answer the other person's question, not yours. You bring a wealth of knowledge to an opportunity, and they find that interesting, but what they want to know is how you help them, how you make their organization better, how you help it grow. Flip it. "If it's all going to be about me, me, me, it's not going to work."
She also sees the common failure. People ramble. They cannot be succinct about what they offer. That is a skill, and it is learnable.
A new chapter may not require becoming someone else. It may require learning how to describe who has already emerged.
The most useful relationships may be ones you already have
When Jackson started asking for help, she went somewhere old.
She had not been connected to the university where she did her MBA. She reconnected, and it opened doors: introductions, opportunities to contribute, people who helped her think differently about what came next. That is what caught my attention in the conversation. We tend to think asking for help means finding new places. She leaned into resources that had been there all along.
She cited a LinkedIn stat that most of us have 200 connections. Her question is the useful one. Have you been in touch with those 200 people? Do they know who you are now?
Jackson also went looking for people three to six years ahead of her. Some had moved through divorce after a long marriage and were past the noise. Others had built coaching practices four to six years earlier. She could see where they got to and how they got there.
Many people hesitate here because they think they have nothing to offer someone further along. Jackson's experience says otherwise. Nobody has told her that. She is trying things they did not try, podcasting among them, and she comes to those meetings prepared. As a connector, she sends introductions back the other way. It becomes a value exchange, and the exchange depends on your approach to it.
There is one more filter she applies. Remove the negativity. Where she lives, who her friends are, what she does with free time. If joy is not written over it, she rarely chooses it. Transition creates space, and space is good, because creativity and thought and innovation live there. Negative energy fills a void too, if nobody is intentional about it.
Belief comes before the receipts
The method you used before had receipts. It worked. Then it stops fitting your current reality, and you have to put down a mask that no longer fits your face.
This is where a lot of people get stuck. No coaching roster, so no coaching. No fractional client list, so no fractional work. They want the evidence before they will permit themselves the belief.
Jackson could not point to years of coaching clients before she became a coach. Brand marketing work was drying up as AI moved through the workplace, and she asked what plan B was. She had always managed large teams. Developing people was the part she loved. A career coach had told her years earlier she would be good at this, and at that point she was not ready to leave.
So she went back to school, funded partly by her package. A six month intensive program at a large university in Toronto. Then a hundred coaching hours, which meant finding 23 people to coach. Then a test. Most people take eighteen months to two years. She did it in a year and thought that was too long.
The evidence came after the decision. What she had in the meantime was a story told from experience that already existed. She had managed people. Developed teams. Built brands. Worked across cultures. Coaching was new. The raw material was not.
She is careful about the other trap. Someone at manager level applying for a CEO job will not get looked at. Someone at manager level with retail experience from high school, or real expertise in cooking, applying to a packaged goods company where that connects, is telling a story that holds.
And her advice for people who are not landing is direct about where to look. It is probably not that you are not capable. It is how you are presenting yourself, how visible you are, and who you are asking. Sitting at home applying to jobs on LinkedIn does not move anything. Get out and talk. The confidence builds through the talking.
Build the next chapter around what fills you up
Jackson kept returning to joy, values, curiosity and experience. That sounds soft until you see how she used it to make hard decisions.
When the marital home sold, people told her to move in with her mother. Free rent. It was the house she grew up in, and her mother at the end was not the person she remembered. It was not a joyful place. So she spent money she did not have to spend and rented in Yorkville for about five months, until she bought something. She would finish work, be a tourist in her own city, visit her mother, spend real time with her, then go back to her own place. The joy was the thing that made the caregiving sustainable.
Later she cycled the Northern Adriatic with her cycling partner, Italy to Slovenia to Croatia and back. She tells her kids to skip the steak restaurant and go for a hike instead. Experiences over things, memories over objects, family at the center of both. Travel started at five years old because her parents traveled, and curiosity about other cultures came with it.
The same point applies to work. We spend more time at work than with friends and family, so it has to align with your strengths, your values and your passion. A founder picking the next chapter only on compensation, status or familiarity may rebuild the exact structure they were trying to leave.
She also noted the people who stay put because they are scared, and she leaves them with a move. You can introduce elements into the role you already have. Organize events if that is your thing. Shadow the analyst if data is. She did it herself as a regional sales manager. Someone told her six months in that they would have applied for the job if they had known it looked like that. Her answer: the job on paper was not this. She brought what she enjoyed into it and got support to do that.
What to do with this in your business this week
If you are between chapters, or watching someone on your team go through one, here is where the conversation starts.
Write the inventory before you write the plan. Strengths, lived experience, values, relationships, interests. The first question is what you have already earned that you still want to carry forward, rather than what job you can get.
Find three people three to six years ahead of you. Peers will not do here. Look for people who have already crossed the thing you are in. Come prepared with how you might help them, and ask for the view from where they stand.
Pick ten names from your existing contacts and reach out this week. Old network, dormant relationships, the university or firm or team that already knows part of your story. Jackson's doors opened from one reconnection she had let go quiet.
Write the paragraph about what you do now, and make it about them. Two or three sentences. What you offer, why your experience matters, how it helps the person reading it. Then say it out loud to someone and notice where you ramble.
Name one thing on your calendar that gives you energy, and protect it. What fills you up is data about the life you are building.
Then take one step before the roster exists.
The Napkin Moment
If Lauragaye Jackson had to write this on a napkin, she already did:
“Starting over? No. Starting from experience.”
It is a small distinction with enormous consequences. Starting over implies loss of position. Starting from experience recognizes accumulated judgment, scars, relationships, capability, mistakes, and earned confidence as usable assets.
For the entrepreneur or executive entering a chapter that no longer has the old title attached to it, that may be the question worth carrying for a while.
What if the next version of your life does not require abandoning the person you were?
What if it asks you to finally use all of them?
Related Insights
If you are building the next chapter from the experience you already have, this is the work of doing it with people who will challenge how you tell it. Build the Field
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This conversation is part of the Exits, Freedom and the Second Stage Growth Hub. See every Growth Hub.
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