A

sher, my only son, wasn’t just an employee. Officially he was “Vice Director of Vision and Operations” or something, whatever we decided to call it, but, as everyone knew, he was poised to take over the business when I retired someday.

He did a lot of networking and outreach, netting new corporate accounts, and I tried to take every opportunity to show him the ropes, help him learn the ins and outs of managing the company, so that when the time came, everything would go smoothly.

“Hi, Asher, how are things going?” I greeted him as I came into his office. It was smaller than mine, but somehow looked larger, maybe because of the sleek, minimalistic furniture and the clean, empty walls. I wondered if he would ever put up framed pictures and certificates, anything, like I had.

He looked up from his screen, startled, and clicked twice, like he was minimizing the tabs he had open.

I settled into the second chair in the room. “Have a few minutes? I wanted to discuss the contract with BrightBox. And some other things that have come up.”

“Sure, of course,” Asher said, but he sounded distracted.

“Want to meet a little later? Were you in the middle of something?”

“No, no, it’s fine. I’m with you.” Asher turned his screen a little and opened up his work email. “Ah, I see, it’s this email you wanted to talk about?”

“Yes. And also, the survey results, the one that we sent out to 2024 clients….”

“Oh, right. I saw you forwarded them to me. I didn’t get a chance to review them yet.”

I frowned. Asher wasn’t himself. His mind was somewhere else. Was something going on?

But I didn’t want to pry. Here, we had to keep things professional. If he wanted to tell me, he’d tell me. Right?

T

he next morning, I settled into Dr. Fink’s waiting room with a sigh and looked at my watch, smiling at the doctor when he came to call me. He’s been our family doctor for years.

“Good to see you, Mr. Steiner. How have you been?”

“I feel great, baruch Hashem. Couldn’t be better. You know it’s my wife who insists I come for checkups.”

“Everyone should have a wife like yours. Nu, let’s do this.”

Dr. Fink took his time on the checkup. Too much time, in my opinion. I was itching to get back to the office. Things to do, people to meet, and all that.

“Well,” Dr. Fink said, finally. “Your blood pressure is higher than I’d like. Last time it was borderline, wasn’t it?”

High blood pressure?

“Ah, it’s probably just because I’ve been running around and around, that’s all,” I said.

“Maybe, but it’s not just the blood pressure,” Dr. Fink said. “Your cholesterol has crept up since your last visit, and the stress markers in your bloodwork are elevated. Nothing dangerous yet, but I don’t like the trend I’m seeing.”

Oh. I breathed in, then out. I felt fine. Or did I? Was that a tightness in my chest, or was I imagining it?

“Shimon, you’re running your business like a young man, but if you want my advice, you need to slow down a little. I know you’re still heavily involved in the day-to-day — but all the pressure, long hours, stress — it’s taking a toll.” Dr. Fink leaned forward, earnest now. “I’m talking to you not as your doctor, but as a friend who cares. You might not feel it now, but high blood pressure and elevated cholesterol are silent risks. You need to make some lifestyle changes to enjoy, b’ezras Hashem, many happy and healthy years with nachas from your family.”

I hadn’t expected that.

“Lifestyle changes?”

“Yes. Exercise, changes to diet — and stress management. And if you can start thinking about retirement, scaling back work to part-time or even giving it over entirely — I would strongly recommend that.”

“Scaling back, huh? My wife will love this,” I said, half joking. “You sure she didn’t put you up to this?”

Dr. Fink smiled, but his eyes stayed serious. “I assure you this is my own recommendation. But let me add that I think you deserve to enjoy this stage of life. Go on vacation with your wife. See the grandkids. Don’t work so hard. Leave that to the young ’uns.”

Vacation. When was the last time we did that?

I’ve always been so busy, busy, busy. Building the business from the ground up was a 24/6 endeavor. And then running the company as it grew and expanded….

I assured the doctor I’d think about it and left, his warnings ringing in my ears.

M

ira, of course, was delighted. It’s like my high blood pressure was her early birthday present.

“No, Shimon, of course I’m not happy about your health risks. Not at all. But the doctor said if you make these changes it should be fine, right?” she said, all in one breath. “And just think of it! We’ll be able to go away together. Take a break without bringing your entire business along. Visit the girls in Eretz Yisrael…” she trailed off, clearly already on the plane.

I held up a hand. “Not so fast. I still need to phase things out, hand everything over to Asher. But yes, if I move my involvement in the business down a notch… go more part-time… it will make a big difference.”

Mira sighed in rapture. “I can’t wait,” she said.

The next week, I asked Asher to come in for a formal meeting. I’d spent several sleepless nights tossing and turning, but by now, I’d made my decision. I couldn’t put my health at risk. It was time to hand over the reins.

Of course, the transition would take time. We’d have to create a plan for a gradual change of roles, and I wanted Asher involved in the planning process. It was going to be his business soon, after all.

Asher walked into my office, and I launched right into things. “So, you know the plan has always been to have you take my place in the company, when the right time came,” I started, almost irrelevantly. Of course he knew that. But Asher just shifted uncomfortably.

I blinked. Maybe he hadn’t realized it could happen so soon? Didn’t feel ready?

“I know you’ve only been here a few years, but Asher, I think you’ve got what it takes. The employees like you, you have a good grasp of the business, you manage clients well, and I have full confidence that when I retire, the business will be in good hands.” I smiled warmly, but Asher looked dumbstruck.

“Are you… planning to retire — soon?” he asked, finally.

I inclined my head. “It seems so.” I told him briefly about my doctor’s visit the week before.  “I hadn’t been planning on doing this just yet, but apparently, it’s time.”

“Oh,” Asher said. His voice was a little hoarse. “I guess — can we talk about this tomorrow? I need to think about it.”

Think about it?

What was there to think about?

Possible scenarios flitted through my mind. Were Asher and his wife struggling with something? Did he not want to take on a higher-pressure job right now? Was there something we could help him with? Why didn’t he just tell me what it was? By the time Asher knocked on my office door the next morning, my nerves were shot.

“T

atty, I feel so bad to break this news now,” he said, taking the seat opposite me and resting his hands on his knees. His words were rushed, like he was reading off a script. “I wanted to — I thought we had some more time before you would want to step out of the business. I was hoping to give you time to train someone else in — ”

Train someone else in??

Alarm bells screamed in my mind, and I braced myself.

“I’ve made the decision that I can’t take the role of CEO. I can’t stay in the business long term,” Asher said. He was looking away now. “It’s an amazing company, and you built it up from nothing, and that’s nothing less than incredible. But it — it just isn’t working for me. I don’t have the excitement that you have dealing with stationery imports and suppliers and clients. There’s a business I’ve been researching, someone who wants me to partner with him to launch something very new and — it seems — very profitable. And I’m going to be doing that.”

I looked at Asher and couldn’t think of a single thing to say.

I’ve been in business for forty years. Handled crazy clients and suppliers who took my money and went AWOL. Dealt with customs mishaps and audits and shipping disasters and whatnot — but nothing has ever left my utterly speechless.

Until now.

I think it took a full minute before I could speak.

“Asher,” I said, finally, when the weight and finality of his words actually sunk in. “Asher — you can’t be serious. This is our family’s business. I’ve been grooming you for this role since day one. I mean, you knew when I brought you into the company that the plan was for you to take over when the time came.”

“I know, Tatty, and I’m sorry, I really am,” Asher said, his knuckles white. “I thought I would do this my whole life, like you, and I planned to. I came to work every day determined to do good things for the company… and I think I’ve done a lot of good work in my time here. But it’s not making me happy. I can’t see myself staying in it for life. I can’t run a business that I don’t feel passionate about.”

“Passion? Since when does business need passion?” I retorted. “We’re talking about a stable, solid company that brings in excellent returns and has been supporting our entire family. It’s a legacy, a family business that can go on supporting you and your family, a gift I’m giving you so you shouldn’t have to do what I did — build something from scratch, with all the risk that entails….

“Do you even realize what you’re saying?” My voice climbed. “You want to give up this — an empire, a successful business that’s ready for you to take over — for a maybe yes, maybe not, startup that’s competing with tens of others out there? Why? How can you even think that’s a responsible move?”

Asher’s hands clenched even tighter. He looked helpless.

“I know it looks irresponsible,” he said quietly. “I know it’s not what you wanted. But this is what I decided is right for me. ”

I breathed heavily and grabbed onto the armrest of my chair. I couldn’t take it. I just couldn’t take it. Asher silently put a cup of water in front of me, and I made a brachah. What if this was it — the cause of the heart attack I was trying so hard to avoid?

“Tatty, don’t worry. I’m not running anywhere. I’ll stay till we train someone in, I’ll cut my hours slowly. We’ll work it out, okay?” he said, almost pleadingly.

Train someone in?

I shook my head. Who was there? My sons-in-law? Two of them were working with their own fathers, and another one had a well-paying job in another state. The younger two were still learning, and besides, they were so… young. Who even knew if either of them could be trusted to take over a business like this one? And certainly not now, at the drop of the hat.

No, if Asher wouldn’t take over, I would have to sell. To someone outside the family.

And everything I’d worked so hard to build for our family, everything I’d labored and sweated to achieve — would be thrown away for Asher to run after some childish pipe dream of his own.

If I could tell Asher one thing it would be: You’re not just walking away from a great job — you’re turning your back on everything I built to secure our family’s future.

Asher

Meetings. I could never decide if I liked them, because they were a change of pace and the secretary ordered good muffins, or if I couldn’t stand them, because at least in my office, I could listen to a podcast or something when work became too mind-numbing.

It was at one of those meetings, dedicated to reviewing bids from suppliers of printer paper and envelopes, when the message came in. I was listening listlessly to the debate swirling around me, about the benefits of switching to European suppliers versus our regular contact in China. At some point, the topic switched, and Yaakov, the sales manager, began presenting a report showing sales trends from 2024. Apparently, highlighter sales had dipped and sticky notes soared. I knew this was important, but I still found myself hiding a yawn.

I gave a furtive glance at my phone. Maybe one of those new clients I was trying to contact would call and I’d have an excuse to step out of the meeting for a minute.

I had a bunch of messages, but they weren’t from clients. I scrolled through them quickly. Tatty never liked it when people checked their phones during meetings, but I was the boss’s son, the heir, untouchable. Let them think I was taking notes on what they were saying or something.

Shloimy Bernstein had sent me a brief message. Hey, Asher, whatsup, give me a call sometime. Have a potential great opportunity for u.

I was curious about that. Shloimy was a good friend, one of those from way back when. We’d been in yeshivah together, both headed out into the working world around the same time. I’d gone to work in my father’s company, taking on the role of deputy director of vision or development or something that just meant learn the ropes and take over the business someday, while he’d gone out on his own — Amazon sales, e-commerce, something like that. Maybe he wanted to partner with us? Sell stationery or something?

I motioned to Tatty that I had an important call and stepped out the conference room into the hallway. If it were up to me, I’d get floor-to-ceiling windows to let in light and air, but it wasn’t up to me — yet, anyway — and I didn’t think the business could sustain a dramatic renovation in any case. So instead of sunny and expansive, the hallway was a narrow, carpeted, dim space lit by a single yellow bulb. I knew Tatty felt that functional and clean were all that mattered in an office, but sometimes I wished we could create a more up-to-date kind of feeling.

Either way, I was relieved for the excuse to take a quick break. It was a shame I wasn’t enthusiastic about the business like Tatty — he lived and breathed stationery imports and clearly loved what he did. But even after five years working with him, I just wasn’t enjoying what I did every day.

I knew what my father would say to that. Who says you need to enjoy work, eh? Wasn’t it one of those newfangled things, I could hear him saying, the idea that you could combine passion with profession, do what you love and never work a day in your life and all that?

I sighed. Like it or not, newfangled was the reality. And it was no fun sitting every day plowing through work I didn’t enjoy and probably never would.

S

hloimy hadn’t said much over the phone, just told me he’d like to meet, texting me the address of some shared office space building.

“The new one, just past the big mall, you know what I’m talking about?”

I did — I’d seen the ads, showcasing gleaming mirror-shine windows and lots of potted plants. I’d never been inside, though. I wondered how it worked. Each person had their own office, and then what? When did they use the shared space? Wasn’t it confusing, so many businesses under one roof? What if someone was coming in for a meeting…?

Shloimy met me at the door, holding a coffee cup. He offered his free hand for a brief handclasp, and then jerked his head to the huge lobby, dotted with sets of couches. Frum men milled around, some engaged in heated conversations, others on the phone. A few of them were sitting, working on laptops, and several were clustered at the coffee machines on one side.

“Want to sit down?” Shloimy offered.

“Sure.” We found seats in a quiet corner and I looked around again. There was an energy in the air — voices, laughter, the feeling like this light, airy, expansive space was a place where things got done.

“You work here?” I asked.

“Here here? I mean, I have an office, we all do. But the lobby’s where it all happens. It’s great, so many contacts in one place, there’s always someone who knows someone….”

Wow.

I shouldn’t be jealous of these guys, I knew. After all, they were all trying to make it on their own, and I had a plum job, and a business to inherit. But….

“Anyway, here’s what I wanted to talk to you about. I’m going into something new, on the side, and it’s big. Credit card processing. It’s a lucrative field, but I can’t go in it alone, I need a partner. I have the capital, but I need someone with a business head to take the lead, manage the operations, get out there and make sales. I know you, you have the experience. What do you say to getting in on this?”

For a moment, I felt a flare of interest spark. But just as quickly, it fizzled out. “Shloimy, you know I can’t, I work with my father.”

“I know, but please, what does he do — sell stationery? This is different. It’s recurring revenue — every time someone swipes a card, we make money. You’re not just selling something once, you’re getting a piece of every transaction, every day, forever. It’s not about inventory, it’s not seasonal — it’s about getting in on the systems that everyone relies on and barely even thinks about. You take a cut of the entire economy.”

Shloimy was passionate, and he’d clearly done his research. And to be honest, all this kind of excited me. Starting something new, something super scalable… something I could take a real lead in from the ground up….

“I don’t know…” I said, slowly.

“Think about it, okay?” Shloimy got to his feet and waved to three men near the front door, just as a delivery guy with a motorcycle helmet walked in carrying several bags of takeout. “Oh, here’s lunch. We’ll be in touch, okay?”

I left with the delivery guy, the tantalizing aroma of schnitzel sandwiches and fries and the sound of banter and laughter following me back to my car.

I

tried to describe the atmosphere to Dini later.

“I can’t really describe it. But it was good. Like real energy. All those guys there… they’re building things. There’s potential, there’s growth. And I think Shloimy’s onto something, something that could really make it big in the future. Not dealing with imports and sales and the same thing we’ve been doing since the 1990s. This is — it’s a business with a future.”

Dini spooned salad onto her plate and passed me the burgers. “I didn’t realize you wanted to leave your father’s business.”

“I didn’t. I don’t, really. I feel bad to… he’s done so much for me, for us. And it’s a solid business. But….” I shook my head. “I don’t know. There’s something about the challenge of building something new that speaks to me, more than just continuing to manage the business that my father is so passionate about, but honestly doesn’t interest me that much.”

“So leave the business,” Dini said. “You can give notice and leave, can’t you? People do that all the time. Why don’t you leave and start your own business with Shloimy?”

I stifled a smile, then sighed. Dini’s impulsive reaction was so predictably Dini, but this time, I felt the same way. “Part of me would love to do that, but my father… he would be devastated. He’s sure I’m going to be taking over one day.”

Dini leaned forward. “But you don’t want to! You’re not enjoying it there, and you’re the one who’s going to be doing this work for the next 35 years. Don’t you need to think about what’s best for you?”

T

he question echoed in my head for the next two days.

What was best for me?

I’d always thought I was lucky, being born into opportunity instead of having to struggle from the ground up like Tatty had. And I was. But maybe… maybe I could have a good job that I also loved and was passionate about?

Shloimy had taken to texting me at least once a day. Research, figures, projections for where this new business could take us….

I reviewed the data. It was sound; we could do this. He had the startup capital, we would need to work hard to build up a client base, but it could really become something big.

It took a little while, but I made the decision. And the first step to cement it was renting an office of my own in the building where Shloimy already worked. I would start there part-time while phasing out of my role in my father’s business. I knew I wanted to stay on until we trained the new hire in; it wouldn’t be fair not to. But as soon as I could… it was time for me to go into something new, something that would energize me, not make me feel like I was suffocating each and every day, stifled in an office and business that just wasn’t for me.

When the email with the office space contract came in, I felt a frisson of excitement. I could do this. I needed to do this.

But I couldn’t sign anything without telling my father.

Thank you, I’ll be in touch, I replied to the email. I knew I was going ahead; I just had to hand in notice here, first. And make a plan to phase out gradually, train in the replacement….

I wondered who it would be. Maybe Tatty would bring in one of my brothers-in-law instead? He’d always been so happy to have a son who would take over the business — and I was the only son, with five sisters — but still, one of the sons-in-law could work just as well. Maybe Debbi’s husband Yoni, they would probably move back from Israel soon….

I wanted to take things slowly, plan how to break the news. But then, suddenly, Tatty started talking more seriously about retirement.

It was strange, really. My father had always been a full-steam-ahead sort of man, always running, never stopping. I never actually imagined he would really retire, and certainly not just yet. But all of a sudden he was calling me in, talking about lifestyle changes and needing to cut back and work less and it was time to move on, and how he was so happy the business would be in good hands—

Oh no, oh no, what terrible timing.

“Can we… can we talk more about this tomorrow?” I asked in desperation, when he called me in for a meeting, apparently to discuss his imminent retirement — and my imminent takeover.

He looked surprised, but agreed.

That gave me 24 hours. Just 24 hours to figure out how to break the news to my father.

Tatty, I’m so sorry, but I’m going out my mind with boredom here?

Nope.

You see, I just need to work somewhere with people my age, good coffee, takeout, and good views?

Nope again.

And it wasn’t really the point, either. Those were perks, sure, but the real thing — the real thing was my need to find a direction that spoke to me, that challenged me. To build something of my own that felt right for me, today, not for my father, forty years ago.

I tried my best. But is there any right way to share such a decision?

“I’m so sorry to break the news now,” I said, praying that my voice would hold steady. “I thought we had some more time with you at the helm… I was hoping to give you plenty of warning so you could train someone else in. But I’ve made the decision, I can’t do this long term.” I took a deep breath, and then plowed on. “It’s an amazing business and you built it up from nothing, and I can’t tell you how much I admire that. But it isn’t working for me. I don’t have the excitement you have.

“There’s a business I’ve been researching, someone who wants me to partner with them to launch something new. It looks like it has a profitable future, and it’s something I’m very excited about. And… and I want to be doing that.”

It was as bad as I’d expected.

First there was the mussar talk about responsibility and hard work and how making a living is not supposed to be fun.

I knew my father would react like that, and I knew how painful this must be for him, but I also knew that what he saw as a jewel, an empire, I saw as a solid, good business, yes, but one with little scalability and a future that, at best, would entail doing the same thing for the next forty years, with similar profit margins. At worst, as the world turned more and more digital, it could become less and less profitable… but I knew Tatty wouldn’t see it like that.

“Stationery is a basic. It’s something everyone needs, always,” he liked to say.

But we weren’t living in the 1970s anymore. And the world was changing.

Of course, a new business was a risk. Everything big came with risk factors. But I was willing to jump in and try, because I needed something to change.

Dini cheered me on all the way, but I felt terrible about how hurt and upset Tatty was.

And then Mommy called.

“Asher? Asher, what happened? Tatty is beside himself. He’s broken. You know the doctor is worried about his heart… that’s why he’s retiring now… and he’s mamash devastated! This is his business, his whole world! I don’t understand how you could do this….”

I bit my lip. I hated, hated, hated this. I’d made both my parents so upset — and I understood them, they had reason to be. But what could I do?

“I’m sorry, Mommy. I know. I wish it could’ve been different,” I said. Beside me, Dini gave a vigorous nod, her eyes wide and sympathetic. “I’ll do what I can to ease the transition. I’m not leaving tomorrow, and I’ll make sure the company is in good hands when I do phase out of my role. We’ll take it slowly, it won’t happen all at once. We’re going to figure this out so everything works as smoothly as possible.”

I meant it. I didn’t intend to leave anyone in the lurch, and I would start out working with Shloimy part time before leaving entirely. But I couldn’t stay in a role that was draining me of energy. And ultimately, wasn’t it better for my father, too, if the person who would take over his business would be really passionate about building it?

If I could tell my father one thing it would be: I wish I could do this for you, but if I can’t stand behind the business I’m leading, it’s not good for anyone. I need to be somewhere I thrive. 

(Originally featured in Mishpacha, Issue 1046)