3,000+ AI tools. 1000+ prompts. All from one newsletter.
Most AI resources are scattered, untested, or buried behind a paywall.
The Shift puts it all in one free newsletter, covering what’s new, and what practically works under 5 minutes a day.
A vault of 3,000+ vetted tools so you’re never guessing. A 1000+ prompt library for every use case you’ll actually hit and free AI courses that make sure nothing stays theoretical.
Plus, right now, 3 subscribers win a free 1-year Claude Pro subscription just for signing up.
In partnership with
These 7 Stocks Are Built to Outlast the Market
Some stocks are built for a quarter… others for a lifetime.
Our 7 Stocks to Buy and Hold Forever report reveals companies with the strength to deliver year after year - through recessions, rate hikes, and even the next crash.
One is a tech leader with a 15% payout ratio - leaving decades of room for dividend growth.
Another is a utility that’s paid every quarter for 96 years straight.
And that’s not all - we’ve included 5 more companies that treat payouts as high priority.
These are the stocks that anchor portfolios and keep paying.
You can download this report for free as of today, but it won’t be free forever.
This is your chance to see all 7 names and tickers - from a consumer staples powerhouse with 20 years of outperformance to a healthcare leader with 61 years of payout hikes.
The Observation — October 2026
I can be experienced at running a business and still need someone to explain how a new system works. Both of those things are true in the work I'm doing now.
After years of running a mortgage company, I know what it takes to carry responsibility for customers, employees, decisions, and the work that has to get done whether the day goes well or not. I also spend time learning tools and processes that weren't part of that business. My experience helps me understand what I'm looking at. It doesn't mean I already know how everything works.
That is a strange place to stand when you've spent years being the person other people come to for answers. You have something valuable to contribute, and you have questions. You can understand a business problem very well and still be new to the room where you're helping solve it.
I recently saw a post asking whether people felt like the odds were stacked against them. My immediate answer was no. I feel like life keeps giving me things to notice, people to learn from, and opportunities I would have missed if I were only looking for the life I expected to have.
That doesn't mean everything that has happened to me was good. There are things I would change immediately if I could. I have also made mistakes, closed a company I spent years building, and had to figure out how to live inside circumstances I never would have chosen.
But I am still here, with work to do and people I love. I want to understand what is possible from here. I keep coming back to two questions: What do I need to learn from this? And what do I do now?
The answers are usually more specific than the story I've been telling myself about the whole situation. They lead to a conversation, a decision, a number I need to look at, or something I need to learn. That's where I want to spend this month's Observation.
WHEN EXPERIENCE HAS TO LEARN SOMETHING NEW
A business can become very good at operating in a set of conditions that no longer exists. The team knows the process. The owner knows the customer. People have reasons for doing things the way they do them, and many of those reasons made sense when the process was created.
Then something changes. Customers ask different questions. A new tool changes how long a task should take. The company grows beyond what one person can oversee. A service that used to be easy to explain becomes harder to distinguish from everything else a buyer sees.
The experience inside that business is still valuable. But it needs current information.
Imagine a company getting plenty of inquiries and very few sales. The immediate explanation might be that people are price shopping or that nobody wants to commit. Those are possibilities. They are also conclusions worth checking before the company spends more money bringing more people into the same process.
What are prospects asking before they disappear? Can they tell what the service includes? Do they understand the next step? Is the proposal answering their problem, or describing the company's work in language that only the company uses?
If the team keeps answering the same question individually, that is worth examining. The information may be missing from the place where customers need it. A small communication problem can create a lot of repeated work.
The next action can be concrete: read the last several inquiries, review the proposal, and ask someone outside the business to explain what they think they would be buying. Find out where understanding breaks down. Then make a change you can observe.
An experienced leader should be able to say, “I thought this was working. Let me look at it again.” That gives the organization room to learn without treating every adjustment as an admission that the original work had no value.
This is where I spend a lot of my attention in consulting: understanding what the company is actually responding to, what it may be assuming, and what decision would make the work clearer for the people doing it and the people buying it.
MONEY, HOME, AND YOUR ACTUAL NEXT STEP
Money decisions can become so emotionally large that the practical question gets lost. “I can't buy a house.” “I'm behind.” “I should have figured this out already.” Those statements may describe how someone feels, but they leave a lot unanswered.
What is making the purchase difficult? The monthly payment, the cash needed to close, income uncertainty, debt, location, or the possibility of moving again? Each answer changes the conversation. A person who needs to understand the costs is in a different situation from a person whose current income cannot support them.
You don't have to commit to a purchase to begin understanding the decision. Start with current income, obligations, savings, and the expenses the home would need to fit beside. Include the ordinary life that continues after closing: transportation, food, family responsibilities, repairs, and room for things you cannot predict exactly.
When you are comparing actual loan offers, look beyond the quoted interest rate. Review the total monthly payment, cash needed at closing, loan costs, and any features that could change the payment later. Property taxes and homeowners insurance matter whether they are collected through escrow or paid separately. The CFPB's Loan Estimate explainer and guide to comparing loan offers show where to find those details.
If the numbers don't work, that is useful information. You can identify what would need to change and whether the goal still fits. You may decide to wait, adjust the price range, work on a specific part of your finances, or reconsider the move. The next step should follow from the situation you actually have.
The same habit applies to a household budget. Before deciding that you are failing at money, look at what changed. An expense may have increased. Income may be arriving differently. A payment you barely noticed before may now matter. You need to see the details before you can decide what to address.
I don't want anyone making a financial commitment because a message made them feel briefly optimistic. I want people to understand their choices well enough to make a decision they can live with after the conversation ends.
THE WORK I AM DOING NOW
The work I do now includes consulting, advising, speaking, training, facilitation, writing, and paid AI work. I bring years of business, mortgage, financial, leadership, and customer experience into those rooms.
Some of that work requires learning new systems. Some of it requires recognizing a very familiar problem in a different setting. An answer can sound impressive and still miss what would actually happen inside a business. A process can appear complete and still leave a customer confused about what comes next. A leadership team can agree with the words in a meeting and leave with different understandings of the decision.
Those are problems experience can help identify. They also require listening closely enough to avoid assuming that a new situation works exactly like the last one.
I am interested in the point where the explanation stops matching what people are experiencing. That is often where the useful conversation begins. We can look at the offer, the message, the handoff, the decision, or the work the leader keeps carrying personally, and get more specific about what needs to change.
If that sounds like something happening in your company, bring me the situation. I work with business owners, executives, and leadership teams through advisory conversations, consulting, facilitated sessions, and training.
For conferences, corporate meetings, leadership retreats, and podcast conversations, I bring the same connection between business decisions and the people who have to make them work in real life.
THE DYLAN FOUNDATION
Dylan and I had started building a consulting business together before he died. When I talk about the work I am doing now, he is part of that history. He is also much more than the beginning of a business or the reason for a foundation.
He was my son. He was funny, creative, loving, and a whole person with a life of his own. I want the things that carry his name to remember him that way.
I wrote last month that I do not believe Dylan had to die for something else to be created. That remains true. The Foundation gives me a place to continue putting love, remembrance, writing, and generosity into the world in his name. It does not explain or justify his death.
Love Doesn't End, Dweewoo, and the work connected to his memory are part of what already exists. Other parts can grow carefully. I care about the work being honest and worthy of him, and I want people who encounter his name to understand that there was a person here who was deeply loved.
THE OBSERVATION ROOM
This week's conversation, What Do I Do Now?, begins with the question that prompted this issue: do you feel like the odds are stacked against you?
In the episode, I talk about what happens after a rejection, what it means to be experienced and still be a beginner, and the difference between helping someone see an option and trying to make their decision for them. I also talk about Dylan, the life I expected, and participating in the life that continued after he died.
The practical thread is how to get from a very large explanation of your situation to something you can actually work with. A job rejection doesn't tell you everything about your future. A business problem needs a closer look than “nothing is working.” Learning something new does not erase the experience you already have.
If you've been turning the same situation over without finding a next step, this is the conversation I made for you. The newsletter gives us room to apply it across work, home, and money; the podcast gives me room to talk it through with you.
YOUR TURN
Choose one situation you have been describing in very broad terms. It might be a problem at work, a decision about money, or something new you want to learn but keep putting off.
Write down what you actually know about it. Separate that from the explanation you have added. If someone said no, what did they say no to? If the numbers don't work, which numbers? If you feel unqualified, what part do you need to learn?
Then choose something you can do with that information. Ask for feedback. Review the costs. Find the person who can explain the part you don't understand. Make the change you already know is needed and pay attention to what happens afterward.
You may discover that you need a different plan. You may discover that the next step is smaller than you made it. Either way, you will know more than you did when the situation was one large conclusion about your life.
Reply and tell me what you are noticing. I am interested in the actual situation, including the part you haven't figured out yet.
MICHELLE VAUGHN CO.
STAY CONNECTED
Thank you for reading The Observation. This monthly letter gives me room to connect business, leadership, money, home, technology, grief, and the things I notice in ordinary life.
If someone came to mind while you were reading, forward this issue to them. You can continue the conversation in the Community and find more episodes of The Observation Room below.
With gratitude,
Michelle Vaughn
Consultant | Speaker | Facilitator | Author