"Can you imagine if someone came to the CRO and said, 'What's your quarterly budget?' and the answer was, 'Well, I don’t really know, but I’m sure it’s fine’?

Mary Shea has raised $80 million in growth capital, led a turnaround as co-CEO, and spent years advising technology companies as a Forrester analyst. She is not someone who guesses at numbers. And yet, partway through a Wednesday Women conversation about leveraging your skills as an executive, she admitted that she and her wife went many years without really knowing what they spent each month. There was always a cushion in the account, always liquidity with the wealth manager, so it never seemed to matter. When it finally did — as they began planning for retirement — untangling it took many months and many conversations.

Mary reflected on this dichotomy and spoke the words that became the through-line of the hour: No company lets a leader run a budget that way. So why do so many executives run their households without the rigor they bring to their work?

The Business of You, an online event hosted by Wednesday Women and brought to you by our longtime partner Monument Wealth Management was a candid conversation to explore this pattern. Moderator and Wednesday Women cofounder Melissa Moody asked three executive members of Wednesday Women to share their experiences and discuss what happens when you turn an executive-level perspective on your own life — and what keeps smart, capable leaders from doing so.

The panel brought three distinct vantage points. Emily Harper, CFP®, Partner and Chief Strategy Officer at Monument Wealth Management, sits across the table from high-achieving families as they try to name what their wealth is actually for. Abi Williams, experienced revenue executive and Founder of Lead Not Lag, spent two decades running revenue at Meta, Oracle, and LinkedIn before redesigning her own life around a three-day work week. And Mary Shea, cofounder and Chief Growth Officer at Meerkat, Inc., has seen a career progress from market leadership roles at Outreach, co-CEO of Mediafly, to now a ground level startup that brings together human relationships with AI to drive growth.

Watch the full event on replay here.

You Can't Build a Go-to-Market Plan Without a Business Strategy. Your Family Can't Either.

Abi spent her twenties and thirties helping companies define their values and build cultures around them. It was in her forties that the obvious question caught up with her. 

"I spend so much time as a leader driving this for companies, for my direct teams, for my organization," she said. "But how about my family?"

So she did what she would have done at work. She sat down with her husband and two teenage daughters, and the four of them agreed on five family values: gift of presence, excellence, fun, health and well-being, and support. Every quarter, they come back to the table and each person names which values they're living well and which need more effort. 

What made it work wasn't the framework. It was how the conversation started. Abi didn't present a plan; she asked everyone, herself included, the same question: How can I be better for you? The answers weren't always comfortable — someone pointed out that she's often on her phone — but they shaped the values. "It's not Abi's plan. It's not the parents' plan," she said. "It's a family plan."

Mary arrived at the same principle from the CEO perspective. Strategy has to come before execution, at home as much as at work. Her wife coined their household's mission statement, that echoes throughout the choices they make as a couple: Do good and have fun.

It sounds almost too simple. In practice, Mary says, it can actually settle a surprising number of arguments — where to vacation, what they spend on, and which companies they're willing to invest in. A mission statement doesn't need to be elaborate. It needs to be specific enough that you can hold a decision up against it and know whether the two match.

Your Energy and Your Needs Drive Your Decisions

If the skills to create vision and strategy are ones we possess, why don't more of us apply them at home? 

Emily's shared data from a study by Total Family, a platform Monument works with, that asked users how much energy each role in their life was consuming. Career came first, at roughly 33%. Friends came last, at 12% — even though 82% of respondents ranked friendship among their five most important things to spend time on.

We know what matters. We just find ourselves spending time elsewhere.

Another barrier that was brought up in conversation is the time horizon. While a business plan may plan for a year or two ahead, a life plan asks you to make decisions today about something 30 or 40 years away. Emily sees this echo in the conversations her advisors have with folk, before purpose before they ever get to investment strategy. 

"You'd be amazed at how difficult it is for people to articulate their goals, their purpose," she said. “Often there isn't a shortage of ambition, just a lack of vocabulary for it.”

Mary's advice for getting past that blank page came straight from the technology sector, where few companies still trust an annual plan. She urges people to:

"Ink it, get it down, and then iterate.” 

What you want at 35 won't be what you want at 55, and a plan you revise isn't a plan that failed.

Abi suggested a different starting point altogether: skip the goals and ask what kind of life you want to live. For her, the answer changed as her daughters grew. When they were small, they needed to be fed and put to bed, and she could travel. As teenagers, they need conversation and mentorship, and a mother who isn't coming home drained. She found the clearest motivation by picturing the alternative. 

"I don't want to go into my sixties so stressed out, so burnt out, unwell, with so much money and not even the energy or the health to spend it."

Emily brought another perspective that supports this thinking. Her most useful executive skill at home is discernment — the ability to tell which good ideas are worth pursuing. As an eldest daughter and a self-described people pleaser, she has had to make hard decisions and then practice a phrase that doesn't come naturally: ‘No is a complete sentence.’

"As we become more successful, that often creates more options for how we spend our time and our money," she said. "Just because you can do something doesn't mean it's the right thing for you." 

Your First Team Doesn't Need to Agree. It Needs Transparency.

At work, "first team" means the peers who sit at your level: each owns a different part of the business, and each knows what the others are trying to achieve. One attendee put it succinctly in the chat: she's a CRO, and she doesn't want to be the CFO - but she SHOULD know what the CFO's goals are. The panel explored what that model looks like at home- both what works and what can go wrong. 

Mary was candid about what goes wrong. She and her wife have been married 30 years and share the same big-picture values, but they spent a long time disagreeing about "the number" — the point at which they'd have enough to work only by choice. "We both kind of believe we're the smartest gal in the room," Mary said. What has helped is an advisor who brings the data, and a habit of talking things through between themselves before they get on the call. Her advice: "Don't be afraid of the friction. You have to have the conversations."

Emily said that kind of misalignment is common, and that it often appears gradually. Couples who agree on everything at the start may change as people, and may see their priorities drift. She recommends repeating values exercises rather than treating them as a one-time event, for each individual as well as for the family.

And Emily wasn’t shy about calling out the opposite risk: when partner who delegates something entirely. Although there’s nothing wrong with one person leading the household finances, problems may arise when someone delegates not just the administration but all of the decision-making and visibility. Emergencies happen, the capable person may not be available, and partnerships don’t always last.

"You'd be amazed at how many smart, successful, powerful women who have contributed significantly to their household's finances have no idea what the balance sheet looks like."

Her suggested fix is modest: at least once a year, go on a “money date.” This includes a quick state of the union on the accounts as well as a check on the questions behind them. Are we still working toward the same goals? Do we both know what we're doing to get there?

Abi described a version of this that runs on empowerment more than oversight. At work, she believes a strong team should be able to run without her, and she has built her household on the same principle. Her husband handles the logistics, she holds the plan, and her daughters know what's expected of them. "If I'm not around, my husband knows what to do. If he's not around, we're all on it," she said. "There's no one person holding all of the weight."

What Are You Retired From?

When the focus of the conversation turned to retirement, everyone agreed that the concept looks tremendously different than it did 20 years ago.  Each panelist brought their own perspective to the conversation. 

As Mary says she is the closest to retirement, she began by sharing her plan for what she calls a soft "deplaning" - rather than an ending. Her father worked at Polaroid for 30 years, and when he was done, he was done. She expects a longer and more flexible version: work that pays a fraction of what it used to, perhaps a nonprofit leadership role whose mission she believes in, with AI tools doing a large share of the work. Her one practical note: if you want to give back later, start building the fund for it now, so the money is there when the opportunity is.

Emily, focused on health span as much as life span, wants to downshift well before the traditional retirement age and spend her healthiest years on things she couldn't do while working full-time. She additionally raised the idea of philanthropy and how we give our time and talents, not just money, once we are in the latter phases of our career journey.

Abi's answer double down on the value of time. She shared that she doesn’t think of retirement as a destination but rather a balance and intentionality in where she spends her time, even now. Abi works three days a week, chooses contracts that leave room for the gym in the morning, and joins calls her travels around the globe. Freedom over her time, she said, is already part of her week, not something she’s waiting for. But she did share what she says she’s officially retired from:

"I'm retired from drama. I'm retired from company drama. I'm retired from toxicity. I'm retired from the golden handcuffs."

Start With One Assumption, and One Conversation

At the end of the conversation, Melissa asked each panelist for one thing that anyone could do, starting this week to bring their executive expertise more into their daily lives. Here’s what they shared: 

Emily made a very tangible suggestion:  Pick one assumption you're making about your future and challenge it. For example: ‘I have to work until 65. I could never take a six-month sabbatical. I have to keep earning at this level forever.’ You don't need to prove the assumption wrong. Just work out what information you would need to test it. "You might be surprised by the options you uncover," she said.

Mary's answer builds on Emily’s: Don't be afraid to crumple up the plan and start over. Just as we pivot in business, we should be practicing curiosity and resilience in the plans that shape our lives outside of work as well. 

Abi's was the to the point and reminiscent of the ‘put your oxygen mask on first’ lin: “Pick you," she said. For years, many of us have lived for the company, the role, the spouse, the children. 

"You can't pour from an empty cup. When you pick yourself, you’re able to do your best work and serve."

None of the topics discussed over the conversation require skils that we’re missing. Leaders in the professional world already know how to set a mission, build a strategy, read a balance sheet, hold a hard conversation, and plan for the unknown scenario. The real work is deciding that the people at your kitchen table deserve the same strategy you give a board. So call the meeting, open up the conversation that you may have been putting off, and start creating a growth plan for your life that mirrors what you do in the office. 

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The Business of You was made possible by Monument Wealth Management, a longtime partner of Wednesday Women and a wealth strategy firm built for life's biggest decisions. 

Are you curious about the Total Family platform that was shared by Emily Harper — reach out and connect with Emily Harper on LinkedIn to get access. 

And for candid conversation about money and meaning, listen to Between Sips, the podcast from Emily and her colleague Jessica Gibbs. Want to talk with Monument's partners? We'll be glad to introduce you personally.

Need that link again? Watch the full replay here or on YouTube.

Wednesday Women hosts online conversations for executive women across industries. To join the next one, or to learn about the Executive Membership, subscribe here.