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REBOOTING BUSINESS  |  EPISODE 22

Shakeena Johnson on Business Foundations, Focus, and the Long Way Home

Rebooting Business, Episode 22, recorded in the summer of 2020, when everybody was rebuilding something whether they wanted to or not.

There is a particular kind of career that does not look like a career at all while you are living it. It looks like a series of wrong turns taken in good faith, each one abandoned the moment its wrongness became undeniable, until one morning you look back down the road and see that every turn was a decision and every decision was a subtraction, and what is left standing at the end of all that subtracting is the thing you actually wanted. Shakeena Johnson has walked that road, and she can describe the map.

She came to episode twenty-two of Rebooting Business with a résumé that reads like four separate people put in a blender. She was on a law school track for years. She was a freelance writer. She was a paralegal and legal assistant for more than a decade. She was a licensed real estate agent. She built websites. She now coaches business owners, and every one of those earlier lives turns out to be load-bearing.

What follows is that conversation rebuilt for reading, with the record checked and corrected where correcting was warranted. Every audio and video link from the original post is preserved below, across every platform the episode was ever distributed on, so that if any one of them disappears the others remain.

The Long Way Home

The law school plan died on a technicality of geography. She studied for the LSAT, sat it more than once, and scored well enough to be accepted by several schools down the East Coast but not well enough for the ones near home. She had a grandmother she wanted years with, and Pennsylvania was where those years were.

She ended up passing a few years later, but I was glad I made the decision to stay.

That is the whole ethic in one sentence, and it recurs. What came next was not drift but method. She called it deliberate soul-searching, and she described it as a process of elimination rather than a search for a calling.

I realized I didn’t want to write for other people. I realized that the things I didn’t like I could just kind of took them off my list.

The freelance writing had started in college, for the reason most college enterprises start, which is that college students are broke. She loved writing. She stopped loving it the moment somebody else owned the deadline and chose the topic. The business writing survived that culling, because business plans did not compete with the creative part of her the way commissioned articles did. Web design arrived sideways, through a handful of projects that generated referrals, which generated more projects, until a hobby had quietly become a practice.

On Writing Things That Carry Someone Else’s Name

I told her about the book. There is a book on my shelf that I wrote for a marketing agency, and my name is nowhere on it. The only proof I have that it came out of my head is a memo from the agency director congratulating me on the job. I keep it in an interactive résumé because there is no other way to claim it.

Anyone who has worked as a copywriter inside an agency knows the specific ache. You write something you are proud of, it goes upstairs, it comes back rearranged and frequently worse, and it goes out into the world wearing somebody else’s byline. Shakeena named the feeling more precisely than I had managed to in twenty years of grumbling about it.

So it’s almost like giving birth in a more minor lesser role, but it’s this visceral thing from you that you have no credit for, no thank you for.

The Morning the Body Made the Decision

She left the legal world the way a lot of people leave a job they are good at, which is to say the body voted before the mind finished deliberating. She suffers serious bouts of vertigo and dizziness. One morning she went to brush her teeth and found herself on the floor.

I was like, nah, you know what, I’m good. I’m good. My health comes before anything else.

She resigned without a plan for replacing the income. About a month in, something unexpected arrived in the space where the panic should have been, which was the discovery that she genuinely liked the freedom. Nobody was telling her when to wake up. Nobody was assigning her hours in the middle of the night. Roughly five months later the same company hired her back as a contractor, this time on her terms.

The contract ended in the funniest possible way. After about a year, the owner came to her and said he had nothing left to give her, because she had done all of it.

I worked myself right out of a contracting position, and so I always think that’s funny.

She was not alarmed, because she had never let that contract become the whole of her income. She had gone and gotten a real estate license in the meantime, on the reasonable theory that a contract with an end date needs a successor in place before the date arrives. Real estate lasted long enough to teach her that she did not want it, which she counted as a return on investment rather than a loss.

Blue Monday

This podcast started life under a different name. It was called Blue Monday, partly because of a fixation on the color that anyone who has seen this website will already have diagnosed, and partly because of the phrase itself, meaning the dread that arrives on Sunday night and does not lift until Tuesday.

I told her about Les Brown, the motivational speaker I listened to obsessively for years, and mentioned in passing that he had been married to Gladys Knight, which is true. They married in 1995 and divorced in 1997. I then repeated a statistic of his about Monday heart attacks that I should have checked before saying out loud, and the correction for that sits further down this page where it belongs.

The underlying observation still holds, whatever the numbers say. The reason Blue Monday resonated enough to name a show after it is that a great many people spend Sunday evening dreading a building they will walk into for forty more years. I worked in agencies where people came to my desk in tears about it. That is the ambient condition this entire conversation was built to argue against.

My own exit from one of those agencies was less dignified than Shakeena’s. There were rotating swing shifts and impossible deadlines and a wife who was rightly furious about the state I came home in. One day I looked at the team manager and told him I was finished pulling his irons out of the fire, offered a two-handed gesture of farewell, and drove home to order a triple pepperoni pizza and watch the most mindless television I could locate. He asked what they were supposed to do. I suggested they figure it out.

The Summer of Two Emergencies

We recorded in 2020, and the conversation kept snagging on the year itself. Her business barely changed, because a web designer and business coach was already working from a computer at home and meeting clients by video. What changed was everything around the business.

She lives just outside Philadelphia, where the protests were constant and where some of them were peaceful and some were not. Her husband is a Black man roughly six foot one. When he left the house, she worried, and she described with real weariness how many people around her regarded that worry as invented.

So people who never had to go through that, people who don’t understand, like there’s added stress. And it’s amazing how many people think it’s either not a problem, not an issue, people are just making it up.

We both admitted to rationing the news, checking every few days rather than continuously, and both of us arrived at the same bleak observation about the arithmetic of change. I mentioned that I was born around the time Malcolm X was shot, and that the difference between then and now is mostly that a law got passed in between and everybody assumed the law had settled it. She asked the question that has stayed with me since, which was where this era’s Malcolms and Kings are, and why they are so difficult to locate.

I confessed to a related and much smaller failure. I once saw Bobby Seale on LinkedIn, looked at his website, and felt the specific twitch that afflicts every web developer who encounters a site that could be so much better. I emailed him and offered to rebuild it for free. He never replied. I did not really expect him to, and I have mostly learned to bite my tongue since.

Where Your Business Stops and Your Opinions Begin

Asked what business owners should be doing to find equilibrium, Shakeena gave an answer in two halves. The personal half was to use the moment for genuine self-evaluation, to define rather than assume what you believe. The business half was more careful, and it is the part worth quoting to anyone currently deciding how loud to be online.

As a small business owner you are the pulse of the community. You provide services for people in your community and you have to understand that without those people you wouldn’t have a business.

Her position was not that owners should stay silent. It was that they should know what they believe, understand who they serve, and accept that alignment between the two is the actual variable. She drew the line at beliefs that harm other people, and she drew it plainly.

I raised the harder practical version of the problem, which is that everything you publish is permanent. I would generally prefer to be the person who builds the website and writes the content and tunes the search results, and to leave my politics off the page, and I am also not a person without politics. That tension does not resolve. It gets managed, publication by publication, and anyone telling you otherwise is selling something.

You Cannot Build a Business Without Knowing Who You Are

This is where the conversation found its spine. I have advised on political campaigns, and the thing they taught me in messaging training was that the strongest identity wins, not the best policy. The 2008 general election was the cleanest demonstration I have watched in person, with one candidate running on the identity of the veteran and the prisoner of war and the other running on something entirely opposed to it, and the outcome legible in the messaging long before it was legible in the polling. That is my read of it, and reasonable people who watched the same campaign read it differently.

The trouble with brand identity work, whether for a politician or a plumber, is that most people know who they should be and who they would like to be and have never once sat down with who they actually are. Shakeena’s version of this was gentler and more useful than mine.

The journey of entrepreneurship, it’s just that, a journey. And it’s very difficult to know or build a business when you don’t know who you are. That journey is going to bring it out of you.

She followed it with the observation that undoes more small businesses than any market condition, which is that loving the work is not the same as being able to run a company built on the work. Her example was a knitter. Somebody adores making hats and scarves, decides to sell them, and discovers that the business requires marketing and strategic planning and a visionary willing to look further out than the next batch.

Passion isn’t enough to run a business. You still need to know all these other things in order to do it.

Her practical recommendation was to hire an assistant as early as affordability permits, but only after doing those tasks yourself first, so that you know what you are delegating and can tell when it is being done badly.

A Digression About Orwell, Which I Got Wrong

My mother taught English, and I went to college intending to be an author rather than a teacher of authors. I concluded, correctly for my circumstances and incorrectly as a general rule, that the writing life did not pay. The pull never went away. On a free afternoon I still go to the bookcase and decide whether today is Bradbury or Philip K. Dick or Cornel West or Khalil Gibran or Stephen King, and then sit out front and read and scowl mildly at passersby.

In that spirit I offered a version of George Orwell’s life in which nobody knew who he was until a trickle of money arrived from Animal Farm just before he died. The emotional truth of what I was reaching for survives. The factual account does not, and it is corrected below.

Ten Pages, Not a Hundred and Fifty

When the conversation turned to method, Shakeena was blunt about business plans. She used to write the long ones. She does not believe in them anymore, at least not for the owners she works with.

I don’t think you need to have like a hundred and fifty page business plan. I do think you need a very condensed action plan.

Her reasoning is that the long document feeds the exact pathology it is meant to cure. New owners research endlessly, accumulate more information than they can act on, and freeze. She calls it information paralysis, and she named it as a bigger obstacle for startups than mindset, which surprised me.

What she builds instead runs to roughly ten pages and usually fewer. It identifies the ideal client with enough specificity to be useful, which means not answering the question with the word everybody. It maps the buyer’s journey. It settles services, packages, and pricing. Then it establishes three systems, which are the lead generation system, the client service system, and the referral and retention system. Those three are the foundation, and most of her work is diagnosing which of them is leaking.

The plan carries actionable items with a schedule attached, weekly and monthly and quarterly, because a plan without dates is a wish with formatting.

Funnels Are Not Lead Magnets

I asked her to separate two terms that clients routinely fuse into one confusing lump, and she did it in a sentence and a half. The sales funnel is the system you lead someone through in order to convert them into a paying client. The lead magnet is what attracts them into the system in the first place. One is the road and the other is the sign at the junction.

The difficulty is that neither can be copied from anyone else. A furniture warehouse and a law firm do not share a buyer’s journey, and a multi-office law firm does not share one with a solo consultant. Her point was that you cannot design the system until you have located where you actually sit inside the client’s journey, which for most businesses is somewhere in the middle rather than at the beginning.

She credited me with remembering the standard stages of that journey, which run from awareness to consideration to decision. Her caution was that clients arrive having already found those stages on Google, and having assumed the generic version applies to them unmodified, which it does not.

The Overwhelmed and How to Move Them

I told her a story I have told before, and it does not improve with retelling. My wife had been diagnosed with cancer. I had a consultation on the calendar with a lawyer for the same day I was driving my wife to be seen, and rather than reschedule it I took the call from the car in the parking lot while I waited, because I could not go in with her. It was a terrible idea. I was emotionally scattered in every direction at once, and the lawyer spent an hour asking technical questions about search and paid advertising and e-commerce, and at the end of that hour she announced that she was completely overwhelmed and was therefore going to do nothing.

I asked Shakeena how you help somebody like that. Her answer was structural and calm.

I would try to figure out what their three most important goals are, the most urgent pain, and just start from there.

You cannot do many things in a day and you cannot hold twenty goals in a month. So you find the one that matters most right now, and you create momentum in a single direction, and the paralysis breaks because it has been given something smaller than everything to act on. Looking back, I did not serve that lawyer well. I was distracted by something that mattered far more to me than whether she signed, and I have made a certain peace with that, but the conversation would have gone better if I had asked her for three things instead of answering her questions about twenty.

Onboarding, Boundaries, and the Volunteering That Went Nowhere

Shakeena uses a workbook in her onboarding. I use a funnel that filters before it welcomes. We arrived at the same conclusion from opposite directions, which is that skipping the structured intake is how you end up with abusive clients, unclear expectations, and projects that fail in ways nobody can fairly assign blame for.

Every time I don’t require it, it blows up. It blows up.

I can match that with two of my own, both from volunteering. There was an orphanage, I believe in Nairobi, whose work genuinely moved me. I offered to take them to the top of Google, set up their donation e-commerce, and walk them through their banking, on the sole condition that they do what I recommended. Four or five months passed with no word. There was a second nonprofit and a second identical silence. Volunteered work without a structured intake is not generosity. It is an unopened invoice, and eventually you stop writing them.

The boundary question is genuinely hard when nobody is paying. How much is this really going to be. How far do you want to take it. Where do you cut it off. Do you even want to be the person who sets terms on a gift. There is no clean answer, only the observation that the engagements which failed were the ones where I never asked.

Start Small

For organization she mentioned KanbanFlow, which she uses to keep her many interests from colliding, deciding what to do and when so that curiosity does not become distraction. I use a similar board with columns for book ideas and subjects and projects, which tells you something about the difference between a coach and a podcast host.

Her closing advice was the smallest thing she said and probably the truest.

You don’t need to be everywhere all at the same time. You don’t need to post a million times just to get a result. Social media is an engagement tool. You should focus on your foundation first before you decide to conquer the world.

What Has Changed Since This Conversation

This episode was recorded in 2020. Several claims in it have aged, and a few of mine were simply wrong when I said them. They are corrected here rather than quietly removed from the transcript.

Shakeena’s name and company have both changed

At the time of recording she was Shakeena Johnson of JSR Vision. She now works as Shakeena Wheeler and is the founder of The Focused CEO, LLC, a business and executive coaching firm working with CEOs and small teams on systems, leadership development, and strategic growth. Her current site is thefocusedceo.co, and coachshakeena.com resolves to the same practice. The JSR Vision links in the original post are retained for the historical record, but readers looking for her present work should use the current addresses in the links section above.

The Monday heart attack figure is badly wrong

In the audio I repeat a claim, attributed to Les Brown, that seventy or eighty percent of heart attacks happen on Mondays. That is not close to accurate and I should not have said it. The real finding is smaller and more interesting. Research presented to the British Cardiovascular Society, drawn from more than ten thousand Irish patients admitted with the most severe form of heart attack between 2013 and 2018, found rates of that heart attack type highest at the start of the working week, with Monday leading and Sunday unexpectedly elevated as well. Researchers describe the effect as a real statistical correlation with a probable circadian element rather than a proven causal mechanism, and nobody claims Monday accounts for anything approaching a supermajority of cases. Separately, heart attacks rise measurably on the Monday after the spring clock change, by roughly a quarter in one Michigan study, and fall on the Tuesday after the autumn change. The phenomenon is genuine. The number I quoted was not.

George Orwell was famous and prosperous five years before he died

I described Orwell as an unknown who saw only a trickle of money from Animal Farm just before his death. Animal Farm was published in August 1945, sold in the hundreds of thousands, drew excellent reviews, and made him famous and, by his own standards, prosperous for the first time. Nineteen Eighty-Four followed in 1949 and was a larger success still. He died in January 1950 at forty-six. The tragedy is real, but it is a tragedy of a short life rather than of obscurity. He had a decade and a half of published work behind him and two enormous successes in hand when he died.

SCORE is a partner of the SBA, not a division of it

I described SCORE, where I served as a certified small business mentor, as a division of the U.S. Small Business Administration. SCORE is a 501(c)(3) nonprofit and a resource partner of the SBA, funded in part through a cooperative agreement with it. The distinction matters to anyone trying to understand how the mentoring is funded and governed.

Bobby Seale is alive, and Oakland has rightfully honored him

My anecdote about emailing Bobby Seale to offer him a website rebuild has a happier coda than it did in 2020. Seale is in his late eighties and remains publicly active, and in October 2025 the City of Oakland proclaimed a Bobby Seale Day and honorarily renamed an intersection near Martin Luther King Jr. Way in his honor.

The Gladys Knight restaurant no longer exists under that name

I joked about wanting to visit Gladys Knight’s chicken and waffles restaurant in Atlanta. Knight sued to remove her name from the restaurants in 2016 after a dispute with her son, who owned them, and the last of them dropped her name in 2017 following state tax enforcement actions. The Peachtree Street location under that name is closed. The joke, unfortunately, aged into a fact.

The voice message link at the end of the episode is dead

The episode closes by inviting listeners to submit a question through an anchor.fm message address. Spotify acquired Anchor in 2019 and retired the Anchor brand at its March 2023 Stream On event, folding it into what is now Spotify for Creators, and the native recording and messaging tools were discontinued starting in mid-2024. Questions should be sent through the contact form on this site instead.

One tool name is unintelligible in the recording

When asked what she uses for organizing, Shakeena names a tool that the audio does not render clearly, and the automated transcript produces nonsense in its place. KanbanFlow is named unambiguously and appears above. The other name is omitted rather than guessed at.

A note on the two interviews

Shakeena and I recorded twice, once each way. This article covers the Rebooting Business episode in which she was my guest. I was separately a guest on her own show, Building Better Businesses, and that appearance is housed in the section below so that the two do not get confused with one another.

Listen to the Full Conversation

Every platform the episode was distributed to appears below. If one link fails, another should hold.

 

Elsewhere on the Same Topic

Shakeena and I also recorded in the other direction, and she had me on her own show, Building Better Businesses, where we covered getting back to basics, playing the long game, knowing your audience well enough to speak to their specific needs, facing fears directly, learning from failure, and seeing where you are headed before you leap. Her current work and channels are below.

 

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