A conversation with Tomide Awe 🪴 about leaving the impressive path, navigating the messy middle and building what comes next - on your terms.
What happens when the life you worked so hard to build no longer feels like the life you want?
There comes a point in many accomplished women’s lives when the question is no longer whether we are capable of doing the things we once set out to achieve, because by then we have accumulated enough evidence to know that we can work hard, build careers, navigate difficult environments, learn new skills, earn the promotion, take responsibility and continue moving towards whatever the next version of success is supposed to look like.
The much more interesting question becomes whether we still want it.
And if the answer is no, or even I’m not entirely sure anymore, what do we do with everything we have spent so many years building?
That was the conversation at the heart of my latest Starting From Zero Live with Tomide Awe, founder of On Your Terms, and although we were ostensibly talking about leaving corporate life and building a business, what we were really exploring was something much bigger: what happens when an accomplished woman begins separating the life that looks impressive from the life that actually feels meaningful to her.
Tomide knows the impressive path well. She spent around twelve years building a corporate career that included Accenture, an MBA from Wharton, Twitter and eventually Meta, where she worked in product strategy, while also building a multi-six-figure handbag business alongside her corporate career. She had achieved many of the things we are taught to associate with success and had accumulated the kind of experience that could have carried her very comfortably into another senior corporate role.
Then, in December 2024, she had her son, and the experience of becoming a mother was accompanied by something far more frightening because, as Tomide shared during our conversation, she almost died three times during childbirth, an experience that inevitably changed the perspective through which she viewed the life waiting for her afterwards. Two months later, while she was still on maternity leave, she was notified that she was being laid off from Meta.
What struck me was that Tomide didn’t describe the layoff simply as a devastating interruption to an otherwise perfectly planned career, because by then she had already begun questioning what corporate life meant to her and whether she wanted to return to it at all, so an event that could easily have sent her immediately searching for the next impressive company or title instead created the space for a very different question.
What if, rather than figuring out her next corporate move, she began building work and a life on her own terms?
When an impressive life is no longer enough
Very early in our conversation, Tomide said something that stayed with me because I think it articulates a transition many women experience without necessarily having the language to describe it: after everything she had been through, she wanted to stop trying to live an impressive life and start creating one that had meaning for her.
There is an enormous difference between the two, because an impressive life is relatively easy to measure through salaries, promotions, qualifications, companies, job titles, achievements and all the other external evidence we have learned to use as proof that we are doing well, whereas a meaningful life is far more personal and therefore requires us to decide for ourselves what actually constitutes success.
Perhaps that is also why questioning an impressive life can feel so uncomfortable, because walking away from something that is obviously failing is one thing, while questioning something you are objectively very good at, that pays you well and that other people may admire is something entirely different.
There doesn’t necessarily have to be anything dramatically wrong with the life we have created for us to recognise that we have changed inside it, and wanting something different now doesn’t make everything that came before a mistake, nor does it diminish the woman who worked incredibly hard to get there.
It may simply mean that the definition of success she was building towards belonged to an earlier version of herself.
For Tomide, becoming a mother added another dimension to that decision because she wanted her son to grow up seeing that there isn’t only one predetermined path through life, and that it is possible to question the default rather than automatically accepting the next rung of whatever ladder has been placed in front of us.
But recognising that you want something different and knowing exactly what that something should be are, of course, two entirely different things.
And this is where I found Tomide’s story particularly valuable.
The messy middle we don’t talk about enough
There can be a tendency, particularly online, to compress major life transitions into neat before-and-after stories in which somebody leaves corporate life, discovers their purpose, launches a business and emerges six months later talking confidently about why everyone else should do the same, but the reality is usually much less linear and, in my opinion, considerably more useful.
Tomide didn’t leave Meta with On Your Terms already mapped out as the business and community it is becoming today. She needed time to recover both physically and mentally after what she had experienced, and during that period she began writing on Substack because she had thoughts, experiences and reflections she needed somewhere to put, rather than because she had developed a perfectly optimised publication strategy.
She also deleted Instagram because she recognised that constantly consuming what everybody else was doing was giving her more input at precisely the moment she needed enough quiet to hear herself think, something I found particularly interesting because starting again often sends us in the opposite direction, frantically searching for experts, formulas and examples of what everyone else has done successfully.
Sometimes the thing we need most is enough space to discover what we think.
By the beginning of this year, Tomide had started consulting with a friend and they attracted clients, but after a few months she realised that they had inadvertently created something that still felt remarkably similar to the corporate world she had just left, because she was working on things that didn’t particularly excite her while once again being accountable to somebody else.
They decided to stop, with the friendship completely intact, and Tomide moved towards another idea that appeared to make perfect sense given everything she had done professionally: becoming a fractional COO.
She hired a coach to help her develop the offer and create a pipeline, and then, during their third session, the coach stopped her and asked a question that disrupted the entire plan.
Is this actually what you want to do?
Tomide knew she could do it and, more importantly, knew she could do it extremely well, but when she allowed herself to answer the question honestly, she admitted that what she really wanted was to build On Your Terms beyond Substack and turn it into something much bigger.
Her immediate response to that truth was also wonderfully recognisable: she couldn’t do that yet because first she needed to be responsible, build the sensible business, create income and then, perhaps six months or a year later, return to the thing she actually wanted.
Her coach simply asked her what would happen if the thing she really wanted to build could generate the income too.
That question gave Tomide something she hadn’t necessarily realised she needed: permission to imagine that the responsible choice and the desired choice didn’t automatically have to be different choices.
She left the call and spent hours writing down her vision for On Your Terms.
Being capable of something doesn’t mean you have to build your future around it
I think this is one of the most useful parts of Tomide’s story for women who are considering what comes next, because after decades of accumulating experience our instinct is naturally to look at everything we have done and ask what business, consultancy or next career could most logically be created from it.
It is a sensible question, but I no longer think it is enough.
Perhaps we also need to ask whether the thing we are exceptionally qualified to do is the thing we actually want to spend the next ten years doing.
Tomide could have built a perfectly credible fractional COO business from her experience and there is every reason to believe she would have been excellent at it, but being excellent at something doesn’t automatically mean it deserves to become the next chapter of your life.
That distinction matters because so many women reach this stage carrying an extraordinary amount of expertise and then assume that starting again means finding a slightly different container for exactly the same work, when perhaps the more exciting possibility is to ask how everything we have learned could be rearranged into something that hasn’t existed before.
We don’t have to discard the experience.
But we don’t have to carry all of the old rules with it either.
Starting from zero doesn’t mean starting with nothing
When I asked Tomide what Starting From Zero meant to her, I appreciated the honesty of her response because she was careful not to romanticise her circumstances or pretend she had taken an enormous financial leap without a safety net.
Her version of zero was having a blank slate and not knowing exactly what she was going to build or whether it would work, while also recognising that she wasn’t literally beginning with nothing because she had significant professional experience, had been diligent about saving and knew that, if necessary, she had the skills and résumé to return to employment.
As she put it, she had built a foundation that now allowed her to take her life back.
I loved that distinction because I think we sometimes talk about starting again as though everything that came before suddenly disappears, when for women at this stage of life the opposite is usually true.
We arrive at the blank page carrying decades of judgment, experience, relationships, knowledge, mistakes, resilience, skills and evidence of what we are capable of, which means that although the thing we are creating may be starting from zero, we are not.
Perhaps zero is simply the point at which we stop assuming the past gets to dictate the shape of the future.
What if confidence comes afterwards?
Another idea Tomide shared during our conversation was what she calls the bravery ladder, which came from reflecting on the relationship between courage, bravery and confidence.
We so often assume confidence needs to precede action, particularly when we are accustomed to operating in environments where we are already competent, so we tell ourselves that we will publish when we feel more confident, launch the offer when we know exactly what we’re doing, speak publicly when we feel ready or start the business once we’re certain it will work.
Tomide’s perspective is almost the reverse: courage may be something we already possess internally, but it is through repeatedly doing brave things that we accumulate the evidence from which confidence eventually grows.
I think this is particularly important for accomplished women because becoming a beginner again can be deeply uncomfortable when we have spent years knowing what we’re doing, and it is very tempting to interpret that discomfort as evidence that we’re not ready rather than recognising it as a natural part of doing something genuinely new.
Perhaps confidence isn’t what allows us to begin.
Perhaps beginning is what eventually allows us to become confident.
Building in public without pretending you’ve already arrived
One of the things I appreciate most about what Tomide is creating through On Your Terms is that she isn’t positioning herself as somebody standing at the finish line telling everyone else how easily she got there.
Her free writing draws heavily from her own experiences of rebuilding, experimenting and navigating the messy middle, while the paid side of her publication includes practical resources, monthly Decision Rooms where women can work through the next decisions in their businesses, and something I think is particularly valuable: a behind-the-scenes look at what building On Your Terms actually looks like financially and strategically.
Tomide was candid about the vulnerability involved in showing that process because it means being willing to share the months that aren’t spectacular alongside the ones that are, rather than suddenly appearing online with a large revenue number and leaving everybody wondering what happened between the idea and the result.
There is something about that approach that feels incredibly aligned with what I am trying to explore through Starting From Zero too, because I am increasingly less interested in polished stories told retrospectively and much more interested in what happens when women allow us to see the decisions, experiments, mistakes and uncertainty while they are still happening.
We need more examples of women building before the ending is known.
So what does “On Your Terms” actually mean?
Towards the end of our conversation, I wanted to bring everything back to those three words because On Your Terms sounds wonderful as a concept, but the interesting question is what it actually looks like when applied to the realities of money, work, motherhood, ambition, identity and everyday life.
Tomide told me that if I had asked her for her definition of success a few years ago, it would have been heavily connected to achievement, whether through climbing the corporate ladder or reaching significant financial milestones through entrepreneurship, and although money represented freedom, there was still a large amount of external validation woven into the way she understood success.
Today, her definition is much simpler and, I think, much more interesting.
For Tomide, living on your terms involves what she described as a kind of radical acceptance of yourself, where external perception begins to matter less and you become more interested in making decisions because they genuinely work for you and for the people you care about.
She still wants to earn well, travel, live comfortably and have financial freedom, but the ultimate measure is whether she can decide how she uses her time, do what she wants to do when she wants to do it, and afford those choices without feeling financially squeezed.
In other words, it isn’t a rejection of ambition, money or achievement.
It is about choice.
And perhaps that is one of the most useful ways we can begin thinking about what success looks like in the next chapter of our lives: not simply asking how much more we can achieve, but asking what we want those achievements to make possible.
What I Took Away From My Conversation With Tomide
If you are currently questioning what comes next, you don’t need to resign tomorrow, launch a business by Monday or know exactly what the next decade of your life should look like, but there are several ideas from my conversation with Tomide that I think are worth sitting with.
1. Ask what you want before asking what makes the most sense.
The sensible option will often be the one most closely connected to what you have already done, which is why it can be useful to temporarily remove practicality from the conversation and ask what you would actually want to build if you believed it could work, before bringing strategy and responsibility back into the picture.
2. Separate your expertise from your identity.
Everything you have learned is yours to keep, but you are not obligated to spend the rest of your life doing the thing you became good at simply because other people recognise you for it.
3. Give yourself permission to be in the messy middle.
There may be a period when the old life no longer fits and the new one isn’t financially or emotionally secure yet, and rather than interpreting that uncertainty as failure, it may be more useful to recognise that experimentation is often how we discover the shape of what comes next.
4. Be honest about the foundations beneath your freedom.
Tomide spoke openly about savings, professional experience and employability giving her the space to build without immediate financial desperation, which is an important reminder that creating a life on your terms doesn’t require us to romanticise unnecessary risk.
5. Stop waiting for confidence to arrive before you act.
If confidence is built through evidence, then the most useful thing you can do may be to take one sufficiently brave step today and allow the result of that action to inform the next one.
6. Explore before you optimise.
Tomide’s advice to somebody beginning on Substack was refreshingly simple: write what you want to write, give yourself space to find your voice and don’t immediately hand your new beginning over to experts telling you how it should be done.
7. Decide what your terms actually are.
Freedom is an attractive word until we have to define what it means in our own lives, so perhaps the more useful questions are how you want to spend your time, how much money you genuinely need, what you want your work to contribute to your life, what you are no longer prepared to sacrifice and what you want an ordinary Tuesday to feel like.
Perhaps the Goal Isn’t to Become Less Ambitious
One of the things I found myself thinking about after our conversation was whether women like Tomide are really walking away from ambition at all, because I don’t think they are.
Perhaps what changes is that after years of directing our ambition towards goals somebody else has already defined, we begin becoming much more selective about where that ambition goes.
We can still want to build extraordinary things.
We can still want financial success.
We can still want our work to matter.
We can still be incredibly driven.
But perhaps we no longer want any of those things at the expense of having a life we are actually present for.
And maybe that is why the phrase On Your Terms resonates so deeply.
It isn’t an invitation to burn everything down, reject everything you’ve achieved or pretend that responsibility, money and security don’t matter; it is an invitation to look at everything you have built, everything you have learned and everything you now know about yourself, and ask whether the terms under which you created your first version of success should automatically become the terms under which you create the next one.
Tomide is still building hers, which may be the most valuable part of following her story because she isn’t sharing these lessons from some distant point where every question has been answered and every decision has been proven right.
She is building while we watch.
She is experimenting, changing her mind, creating offers, developing her community, sharing what works and being willing to acknowledge what doesn’t, which feels far more useful to me than another perfectly polished story in which the messy middle has conveniently disappeared.
Perhaps that is what Starting From Zero is becoming for me too: a place to document women in motion rather than only celebrating them once they have arrived.
Because at this stage of our lives, starting from zero doesn’t mean erasing everything that came before or pretending we know nothing.
It means recognising that we have accumulated an extraordinary number of pieces along the way and, perhaps for the first time, we get to decide how we want to put them together.
And this time, we get to choose the terms.
You can continue the conversation with Tomide through On Your Terms on Substack, where she shares the realities of leaving corporate, navigating the messy middle and building a business designed to make going back optional.
And after watching our full conversation above, I’d love to hear your answer to one question in the comments:
If you could change one of the terms on which you’re currently living or working, what would it be?
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Outside of Substack, you’ll find me creating Intentional Living Magazine and helping private clients build their platforms through House of Brand.
