Hey, OTB community!
Every few months, I run a “mailbag edition” — where I answer questions from readers. You can read previous ones here and here.
Today, I’m answering three questions…
- How do I find a mentor?
- How long does it take to succeed?
- How do I balance work and kids?
If you ever have questions, just hit reply or email me at hellojasonfeifer@gmail.com.
1. How do I find a mentor?
The first question comes from Anne.
Quick background: Anne and I met at an event many years ago, and stayed loosely in touch over Instagram. Although she’s making a personal request here, her question is rooted in a universal topic — so it’s worth answering for everyone.
Anne asks:
Between becoming a mom and growing my company, I’m at a point where I really need a mentor — someone in my industry who can offer guidance and perspective.
For years, I hoped I would find that person naturally over time, but it just hasn’t happened. I’ve realized I need to stop leaving it to luck and actually go after it. What would you advise me to do? Have you mentored others before, and is it something you’d be open to?
Yes, I have mentored others before. But I didn’t know it.
That captures the complicated nature of this topic, and what I believe is a misunderstanding about mentorship. So I want to unpack this in personal terms — talking about mentors, myself, and even my relationship to Anne.
Let’s start with mentorship. Successful people often give credit to their mentors, and that gets reinforced in stories like this:
As a result, we often think of a “mentor” as a singular person who plays a critical role in our success. We wonder: Why don’t I have that person? Then we hunt for them, as if we’re filling an open role at our company.
This is where the problem begins.
Over the years, dozens of acquaintances and strangers have asked me to be their mentor. And I need to be honest: The question freaks me out. It sounds like a huge commitment — full of emotional labor, unclear boundaries, big expectations, and no clear end date. It’s why I always say no. I just don’t have the bandwidth! And I’m not alone. Many of my peers feel the same way.
But that’s OK. There’s a better way to think about mentorship:
Instead of trying to find one mentor, fill your life with mini mentors.
You are surrounded by knowledgeable friends, colleagues, peers, and acquaintances. Pursue and cultivate those relationships. Identify the ones you can learn from, or who have specific expertise you need. Open up to them. Get vulnerable. See who feels equally invested in you. Lean into the most genuine connections. Maybe even suggest catching up regularly.
This significantly lowers the barrier to entry. Take me, for example. I’ve known Anne for years, and I like her. If she asked me for 30 minutes to catch up, and then asked if she could occasionally text me for some quick advice, I’d happily say yes. She’s very welcome to think of that as mentorship. I just don’t want to sign up for the role.
This is exactly what I’ve done with others. I never had a “mentor” in a traditional sense, but I’ve had lots of mini-mentors who I’d turn to in specific moments of need. I’ve also become the person that others turn to. In fact, many friends and colleagues have said they consider me a mentor — but like I said above, I had no idea! I just thought we were supporting each other. And that’s why it worked.
If you can find a singular mentor, then that’s wonderful. Enjoy that relationship! But if you can’t, don’t worry about it. Stop hunting for mentors. Just invest in your network, and it will mentor you back.
2. How long does it take to succeed?
Last week, I wrote about how to most effectively invest your time and effort.
I said you shouldn’t need to endlessly push to make something happen. Instead, you’ll want to find projects that gain their own momentum.
Menucha replied with this question:
I’ve been taught that “if you try hard you’ll succeed” and “overnight success usually takes 15 years”.
While this hasn’t proved true to me personally yet (I’ve only been at it for 10), I’d love to hear more of your thoughts on grit vs. ease, consistency vs intensity, or delayed vs instant gratification.
This is a great question. Grit is often treated as a badge of honor, but that misses an important nuance.
Consider this story: A founder believes in their startup idea. They push for 15 years, despite hundreds of people telling them no. Then they succeed. “Never give up,” they tell us.
You’ve heard stories like that before, right? They’re inspiring! But I think they’re also a lousy lesson. These stories are basically telling people: “Hard work equals success. So if you don’t succeed, you weren’t trying hard enough.”
That’s nonsense. Remember, for every person who succeeded by never giving up, hundreds of others failed the same way. But you only hear the success stories. It’s confirmation bias.
Here’s the truth: Hard work is an ingredient for success, but it does not guarantee success.
So what does? It’s hard work plus the right adjustments. You need to constantly evaluate your efforts, and then, if you’re not seeing the proper momentum, make smart and educated changes.
Remember Emily Dong, who I wrote about last week? She abandoned two previous business concepts. Her third finally worked. That’s the very definition of hard work — because it’s really hard to walk away from an idea and start again.
Do not mistake “hard work” for “necessary change.” We need both to succeed.
3. How do you stay productive as a parent?
Jenn asks:
I just found out that I am pregnant with my second child and this same week I launched my first website for my small business,
I know those things are unrelated but I am feeling the world swirl around me a bit in a pretty unsettling way (although that could just be the morning sickness). Since you’re 10 years ahead of me on this ride, any advice?
Absolutely!
When I had kids, I thought my career would slow down. I was working all the time — nights, weekends, basically nonstop — and parenthood would severely limit that. I thought less time would mean less progress.
But to my surprise, my greatest professional leaps have happened while I had kids.
How? Because parenthood (like many parts of adulthood) forces us to ruthlessly prioritize our time. When we’re younger, time is a luxury to be spent freely. As we get older, time becomes a precious resource to be spent wisely.
Before kids, I was working a lot… but I realized it was also inefficient, mixed in with all sorts of nonsense like spending hours on Twitter. Then I become much more conscious of exactly how I’m spending my time.
Here’s how: Whenever I’m deciding how to spend my time, I ask myself, “What outcome do I want from this hour spent?”
Acceptable answers could include…
- This time will lead to me making money.
- This time will lead to new opportunity creation.
- This time will strengthen a relationship with someone I care about.
- This time will provide necessary stress relief.
But sometimes, I don’t have a good answer. Watching TikTok? Attending random events? Taking meetings for unclear purposes? I don’t see the clear outcome, so I say no.
This isn’t a perfect system, of course. I’m still often stressed about time. There are still many things I’d like to do, which I can’t. It’s a constant balance. It’s never easy.
But I now believe this to be true: There isn’t time for everything, but there is time for what matters. You just need to define what matters to you.
That’s how to do one thing better.
