People & Culture

The Art of Self-Awareness: A Founder’s Guide to Assessing Strengths and Weaknesses

As a psychologist, Dr. Emily Anhalt is in the self-awareness business — helping folks discover the patterns that are holding them back, and working deliberately to build new ones that fuel success. “The whole concept of self-awareness is that the more you know, the more you realize that you don’t know. Self-awareness is a moving target — there’s always more to understand about ourselves,” says Anhalt. 

You’ve likely come across her Twitter feed, where she regularly drops pearls of wisdom that stop you mid-scroll. As the co-founder and Chief Clinical Officer of Coa, she’s looking to bring her signature concept of emotional fitness to the masses. (And there’s more — we’re eagerly awaiting her forthcoming book.)

Before becoming a founder herself, Anhalt got a unique look behind the curtain at the inner workings of entrepreneurs, spending a decade as an executive coach working 1:1 with founders riding the tumultuous waves of startup life. It’s a perspective that’s given her a deeper appreciation for founder DNA — the very traits at the core of successful founders that enable them to dream bigger, push harder and withstand the naysayers.

But as she’s seen in her practice (and now as a founder herself), it’s a double-sided coin. The very traits that make a founder successful can also hold them back — and, when left untreated, prop up barriers to their teams and companies. “Anything that can be your success can be your undoing. For example, hustling is good. Holding people to high expectations is good. But when does that start to become a problem?” says Anhalt. 

Successful leaders keep an eye on the personality traits that have helped them achieve their success. Strengths without self-awareness become weaknesses. Strengths examined regularly become superpowers.

In this exclusive interview, Anhalt explores this concept further, examining the five common traits and behaviors she sees in successful founders. 

Work is their identity

A greater ability to delay gratification

Valuing autonomy and independence

An equal helping of narcissism and imposter syndrome

Something to prove

She dives into their duality — how each trait can be an incredible buoy when the seas are choppy, and how it can also become an anchor scraping along the bottom, hindering progress. She shares tactical suggestions for each trait so that founders can amplify the positive side of the ledger and mitigate some of the bits that might drag them (and their companies) down. 

WHY THIS WORK MATTERS (ESPECIALLY NOW)

More often than not in her coaching practice, founders aren’t enthusiastic about peeling back these layers. “When I work with founders and I start to poke at these traits, they get worried. ‘Don’t take these things away from me — this is why I’m able to succeed.’ I remind them that I’m not trying to strip away these traits or change who they are. But the goal is to examine when something is helping you and when it’s getting in the way,” she says. 

Dr. Emily Anhalt, co-founder and Chief Clinical Officer of Coa

Of course, there are countless advantages to a founder getting curious and exploring the outer edges of what makes them tick. And these perks trickle down beyond the founder’s seat, permeating deep into the company DNA. “I use the comparison that a founder is a bit like a parent. When you think of a parent who’s never been to therapy and never worked on their own stuff, the kids end up having to do the work on behalf of the parent,” says Anhalt. 

A founder who doesn’t spend time getting curious and trying to grow themselves is not going to create an environment where other people feel like they can get curious and grow.

“I think there are a lot of startup employees who feel like they’re dealing with baggage at the company because the people in charge aren’t dealing with it. By doing that work as a founder, you remove that burden from your team and open up their bandwidth and energy to focus on doing great work and making your company successful,” she says. 

It might sound a bit hand-wavy — but the common refrain of “healthy founders, healthy returns,” isn’t just a kumbaya thing. “Your company is going to be more successful if your employees aren’t spending their time processing your emotions because you don't understand how your actions as a founder are affecting them,” says Anhalt.

And in her view, there’s never been a better time to put this work front and center. “It’s more stressful to be a founder right now. I have so many founders I’m working with who need to go raise in what appears to be a really challenging environment. They say, ‘All of a sudden, overnight, my ARR has to be $10 million instead of $1 million.’ That’s a tough thing to do,” she says. 

So don’t put self-discovery on the back burner until you have “more time” to pick it back up — a pot left unattended might just boil over. Get started by exploring these common traits and patterns of behavior Anhalt often sees in the founders she works with — and her prescription for making sure they’re not secretly holding you, your employees and your company back.

FOUNDER TRAIT #1: WORK IS THEIR IDENTITY

Dr. Anhalt’s definition: The line between a founder’s work and personal life is barely visible, as they’ve tied so much of who they are to the success and failure of our company. As such, it might become all they think and talk about. 

Why this is a strength

No matter the industry, being an early-stage entrepreneur simply isn’t a 9-5 type of job. There are countless things that require attention on the path to product-market fit — from building the product, trying to sell to customers, assembling the early team and strategizing around fundraising. It takes a singular focus and relentless energy to keep up with this intense pace of building from 0 to 1.

“When we care deeply about something, we do better work. Some of the most amazing things in the world have been created by people who are deeply passionate about the space,” says Anhalt. In short — transformational companies emerge when founders obsess about a problem, and how they might solve it.

Why this is a weakness

“Any good financial expert would advise you to diversify for better returns — and that’s also true in our own lives. If we’re completely invested in only one part of our lives, that can become a problem,” says Anhalt. 

Startups are marked by ebbs and flows — the perfect up-and-to-the-right company trajectory is most often a myth that glosses over the grittier details. There will be days, weeks, months — maybe even years — where things aren’t going as well as you’d hoped. 

If founders don’t prioritize having other parts of their identity worthy of their time and attention, it can suddenly feel like their whole life is on fire, versus just that their work life isn’t where they want it to be.

It also impairs your decision-making as a founder. “If it feels like your whole life is on fire, it’s difficult to focus and fix things. You’re in a much bigger crisis mode,” she says. 

And in terms of how you interact with the rest of the team, delegating tasks becomes significantly more difficult when work is your whole identity. “You have a harder time trusting people because now it feels like they’re playing with the fate of your entire life, not just your work. You might find that you become an intense micro-manager,” says Anhalt. 

And when you wring out every bit of your energy into the company, it sends the message to the rest of the team that they’re expected to give just as much of themselves. “I’ve seen a lot of people leave startups because they felt the expectation was that they would sacrifice everything. But the rank-and-file startup employee doesn’t own 42% the way a founder does,” says Anhalt. 

Even if you consider yourself to have a higher threshold for burnout, how do you make sure the rest of your team doesn’t burn themselves out to keep up with you? 

How to protect your most precious resource: yourself

This idea that, as a founder, work should be your whole identity, leads to an all-or-nothing mentality that Anhalt sees time and time again. “They’re either working all the time to the point of exhaustion and where they can barely handle it, or they fear they shouldn’t be a founder at all. That’s not a mentality that will serve a founder — you need to be able to play the long game,” says Anhalt.

She borrows a quote from investor Michael Dearing:

There’s plenty of money in startups and there’s more than enough talent. The true runway that founders run out of is the emotional capacity to handle the grinding gears of startup life. 

Anhalt finds in her 1:1 work as an executive coach, there’s a sneaky undertow that starts to drag you under. “Imagine you’re playing a card game, and the game was going on for a really long time. You start to feel tired and don’t really want to play anymore You might, without even realizing it, start to make less smart moves, just so you can lose and be out of the game,” she says. 

Anhalt sees this same self-sabotage with founders. “They’re so tired that they don’t feel like it’s okay to slow down or prioritize other parts of their life. Instead, I watch them sub-consciously self-sabotage, because it feels like the only way out,” she says. Here’s what that might look like: “They may not send investors the information they need and start jeopardizing those relationships. Or they might start fighting more with their co-founders.” 

Tips to keep burnout at bay:

Far too often, Anhalt finds that founders and startup leaders don’t pay attention to the nagging feelings of burnout until they’re already in the throes of a spiral. “In our hustle-porn culture, no one blinks an eye when a founder sacrifices sleep, skips most meals, or loses our relationships for their company. In fact, it’s celebrated,” she says.

Just as your romantic partner shouldn’t be your only deep relationship, your job shouldn’t be your only passion. Diversify your life for healthier returns.

Instead, Anhalt prescribes a three-step framework for catching burnout as it begins to creep up so you can start taking preventative measures — rather than finally picking up the bottle of vitamins once you’re already down with a bad case of the flu. “Burnout is a lot harder to fix than it is to prevent. Prioritize your health as a business asset,” says Anhalt.

Step 1: Figure out your warning signs. “The early warning signs for burnout are different for each person. You might stop eating lunch, or you might be less patient with people. You might find yourself less excited to get up and go to work, or you might complain more. You may start having trouble sleeping. Spend time digging deep within yourself to understand what your early warning signs are.” 

Step 2: Recruit an accountability buddy. “Find someone to keep an eye out for these signs of burnout. It’s harder to recognize them in ourselves. Ask someone close to you, like a co-founder or romantic partner, to look to see if you start skipping lunch or start complaining more. Create those shock absorbers.” 

Step 3: Take action. When that accountability buddy points out a red flag, listen. “When someone tells you that you haven’t eaten lunch for four days, how do you build in some rest? Is it scheduling a vacation or a coaching session? Is it delegating more or asking a co-founder to give you an assist? Don’t just sit with the information — take action. Stop telling people about self-care and start showing them.”

FOUNDER TRAIT #2: A GREATER ABILITY TO DELAY GRATIFICATION

Dr. Anhalt’s definition: Founders work for 10 years like no one else will so they can live life no one else can. They take smaller salaries and sacrifice relationships for the 1% chance that their company will exit. 

Why this is a strength

The path to a sustaining business is winding — very few founders knock it out of the park on their first idea and instead need to pivot their way around to find something that sticks. And once they reach product-market fit, there’s still a long road ahead to the ultimate goal, with an IPO or a meaningful exit still likely many years away. “Very, very few startups are successful immediately — you’re going to have to play the long game,” says Anhalt. 

And in addition to delaying gratification (like a financial payoff), founders aren’t likely to receive tons of kudos along the way. “My experience, both as a founder and working with other founders, is that people aren’t giving you shoutouts all the time — people don’t know all the hard work that you’re doing under the hood. Investors aren’t giving you a pat on the back for each tiny victory — they’re eagerly looking ahead to the next milestone,” says Anhalt.

Founders are uniquely gifted at putting their heads down and pushing forward without much recognition.

Why this is a weakness

As Anhalt reminds us, “In founder life, every achieved goal spawns five new ones. Founders are notoriously bad at slowing down and celebrating as they go. Yes, they may need less validation than other folks, but as humans, we still need gratification in our lives,” she says. 

“I was working with a founder who had just hit a huge, amazing milestone that he’d been working towards for years as the most important goal. I said in our coaching session, ‘Wow, can we just pause and celebrate this?’ And his response was that he didn’t have time and he was focused on the next milestone that he needed to hit,” she says. 

But eventually, that seemingly endless well of self-assurance and motivation will run dry. “It’s hard to push towards something in perpetuity if you don’t pause and feel proud of what you’ve accomplished thus far,” says Anhalt. 

She also sees founders bring this same tendency to their interactions with the rest of the team. “Founders who don’t believe they themselves deserve recognition for small wins will be less likely to recognize their team. They’re less likely to say good job, or celebrate milestones, like raising a Series A,” says Anhalt.

A mistake founders often make is assuming that because they need less validation along the way, no one on the team needs gratification either. 

How to bring gratification to the grind of startup life.

Anhalt shares advice for founders to tweak their approach to inject a dose of validation for themselves and mete out kudos to others. 

Be your co-founder’s cheerleader. “It can be very lonely to not have your work recognized — but it’s also incredibly uncomfortable to toot your own horn. I recommend that co-founders shout each other out and share with the rest of the team what the other is doing. For example, I will make a point of saying to the team about my own co-founder, ‘Alexa has been working so hard behind the scenes to secure this next round. Here’s everything she’s been doing and it’s been so cool to see her in action.’ That way the rest of the team can share in that pride.”

Make the ask. “Founders are quick to ask for constructive feedback. But I recommend they also ask for positive feedback, too. Ask your team what they think you’re doing well or in what ways they feel supported. What kind of milestones can they not wait to get to? Why are they most excited to work at the company?”

Tell folks they’re making a difference. “There’s a lot of talk about ‘the trophy generation’ and that people just need constant compliments. But I believe it’s the meaning-making generation. Folks want to know what they’re doing actually matters. If not, why are they working so hard? It’s important to help your employees understand that their hard work is being seen and that it makes a difference to the company’s goal. While it’s important to let people know when they need to make a change, it’s also important to cheer when things are going well.” 

People don’t want participation trophies. They want to know that they’re making a difference.

FOUNDER TRAIT #3: VALUING AUTONOMY AND INDEPENDENCE

Dr. Anhalt’s definition: For many founders, the very idea of working for someone else makes their skin crawl. Founders want to be the shapers of their own destinies.

Why this is a strength

When you forgo a traditional career climbing the corporate ladder and set out on the founder's path, you take on heaps of risk and roll the dice in the hopes of creating your own destiny. “Getting to decide what you want your life to look like is a strong pull for a lot of people toward the entrepreneurial lifestyle,” says Anhalt.

As she’s seen in her therapy practice, this is often ingrained early on. “I’ve seen that a lot of the founders I work with are, for better or worse, very independent people. I say for better or worse because a lot of people are really independent because they had to be — they had life circumstances where they didn’t have any other choice, so they learned to be independent early,” she says. 

And this independence can serve you well — because building a startup doesn’t come with a turn-by-turn navigation system. There will be plenty of moments where you have to forge ahead, operating from first principles and marching to the beat of your own drum. 

Why this is a weakness

Even if you’re a solo founder, building a company is not a solo pursuit. You’ll assemble an early team and, eventually, bring on investors and a board. “The downside of that independent streak is not being able to trust other people to support you, and not being able to ask for help, even when you know that you want it or need it,” says Anhalt. 

This impulse can start to creep in particularly when you start building out the team. “We all know that, ideally, you hire people who are smarter than you and better at certain things. But if it feels essential to your identity to see yourself as a person who doesn’t need anyone else, you might unconsciously not want to bring on people who are better than you,” says Anhalt.

Giving away your legos is a tough pill to swallow for just about any founder. “You might see a founder who’s really slow to hire a Head of Product because they want to hold onto that role. They think, ‘product is my background, no one’s going to be about to do it better than me. So I’ll do both jobs,’” says Anhalt. 

But as a company scales, beyond just a few people sitting in a room making decisions, the founder’s role permutates quite drastically. “No one will be doing exactly the same thing two years in as they were when they started. And I’ve seen a lot of founders who resist letting their role change,” says Anhalt.

It's a tough reality that the skills it takes to start a successful company are not exactly the same skills it takes to run a successful company.

How to build delegation and collaboration into your company DNA

Getting over the hump and hiring people for the roles you as the founder are currently playing is just the first step — you’ve got to start letting go of the wheel once they’re on board. You’ll get significantly more out of the folks who join if they feel like they’re a driver, not just a passenger. “Think about it from the early employee perspective: If you work at a company where you don’t think people actually feel like they need you, you’re not going to want to show up really hard. You won’t feel all that needed or important,” says Anhalt. 

As a founder, instead of thinking, “Can I do this by myself?” you should be thinking “Do I have to do this by myself? Or would someone else benefit by taking this on?”

Get comfortable with one of Anhalt’s favorite phrases for founders to lean on: “I trust you.” “When people feel trusted, supported, and empowered, they show up as their best selves and do their best work,” she says.

As a founder, there are a certain set of things that only a founder can do — like fundraising or setting the strategic course for the business. And by delegating most of the other things in the pile, it frees up your time and energy to focus on those things that are unique to the founder’s role. 

Anhalt’s advice here is a bit meta: delegate your delegation. “If you’re not good at asking for help, you should ask people to help you. Start by saying to a co-founder or other leaders on the team, ‘Hey, I’m trying to get better at asking for help. So I’d love for you to check in with me regularly to help me help myself,’” she says. 

As a founder herself, this is something Anhalt’s had to face in her own journey. “It's been important in my own growth for people to say, ‘Emily, you need to let go of this task. You are not the only person who can do this. There are other people on the team who can do this,’” she says. “And to have to face what does it mean about me if I'm not so special that I'm the only one who can do this? I have to accept that about myself so that I can delegate and have things scale beyond me.”

FOUNDER TRAIT #4: AN EQUAL HELPING OF NARCISSISM AND IMPOSTER SYNDROME

Dr. Anhalt’s definition: I call this Narcissimposter Syndrome. Narcissistic defenses are necessary to push toward a reality that no one else sees or thinks is possible. At the same time, most founders are terrified that they have no idea what they’re doing and that they will be exposed at any moment.

Why this is a strength

“Narcissistic defenses get a really bad rap — but there’s such a thing as healthy narcissism,” says Anhalt. Here’s how she sketches out the differences. “Healthy narcissism is when you think highly enough of yourself to think you’re capable of incredible things and hold that belief in yourself. Unhealthy narcissism is when you’re actually deeply insecure and use confidence as a false mask to deny how insecure you feel,” she says.

So while the word narcissism might make folks shudder a bit, it can be a necessary component to weather the storms of founder life. “As a founder, you have to think you’re capable of something even though you’re going to be told ‘no’ at almost every turn. But if every founder who was told that their idea wasn’t going to work didn’t pursue it, we would have no companies,” says Anhalt.

And on the other side of the ledger, imposter syndrome has its own bad rap. But in Anhalt’s view, folks tend to overlook what it brings to the table. “It’s important to recognize that there’s a lot you don’t know. Being a founder is a weird job and everyone’s kind of making it up as they go. There’s no perfect playbook — you need to be able to ask for help,” she says.

In her role as a founder coach, Anhalt is privy to that inner voice. “There’s this juxtaposition of people sharing all their wins and successes on Twitter and outwardly projecting this confidence, but internally not feeling that way. In my practice, I don’t have any founders who feel like they’re crushing it all the time. They’re all struggling, they’re all overwhelmed,” she says.

Why this is a weakness

A healthy dose of confidence is necessary to keep going amidst doubters and roadblocks. But when does it become too much of a good thing? “At some point, you also have to be able to hear if what you’re doing isn’t working. If something needs to change and you need to pivot your product. If people are frustrated with your leadership, you can’t always have the track playing in your head that they’re wrong and you have to keep going. Sometimes you have to quiet that voice and hear what they have to say and make a decision from there,” says Anhalt. 

It’s an ever-evolving process of trying to tune the dial to the perfect level. “The downside, though, is that a lot of founders can start to have intense self-doubt that can be paralyzing,” she says.

There’s often a ricochet thought pattern that founders go through where they simultaneously think they’re amazing and terrible — often going back and forth within minutes.

How to get out of your own head

The antidote here is to bring in a chorus of voices, rather than only listening to one soloist. “The voices in our own mind are not always the truth. Don’t believe everything you think,” says Anhalt.

Ask for feedback: “You shouldn’t be the only one deciding how you’re doing. Actively ask for feedback from the people around you — your co-founders, your investors, your board, the folks on the team you work closest with. Bring in other people to tell you when you’re doing a good job and when you should be doing something better.” (For more here, we recommend this Review article on becoming a feedback magnet.)

Compare notes: “As founders, we’re pretty good at convincing ourselves that we’re the only ones having this much trouble. Building a community of other founders was a major unlock for me. It was a big relief to find other founders who also felt like they didn’t have any idea what they were doing. Phew, none of us have it all figured out and we’re all making it up as we go. People who can say, ‘No, I’m with you. And here’s what I do about that problem.’ Founders need other founders.”

FOUNDER TRAIT #5: SOMETHING TO PROVE

Dr. Anhalt’s definition: Whether they’re trying to prove it to their parents, themselves, or the world, there’s a chip on the founder’s shoulder and they won’t stop until they’ve achieved what they set out to do. 

Why this is a strength

When driving down the company building freeway, there will be countless exit signs encouraging you to turn off the road. But startup lore trumpets stories of the folks who kept their foot on the gas and ignored those exit signs. They might make a U-turn (like Stewart Butterfield pivoting from creating an online game to building Slack or the Notion founders throwing out the code and rebuilding from scratch), but they didn’t get out of the car. “Feeling like you have something to prove, either to the outside world or to yourself, can be an incredibly powerful motivating force and carry us through when things aren’t going well,” notes Anhalt.

Why this is a weakness

But becoming a founder just for the sake of being a founder, rather than an intense founder-market fit or an obsessive focus on solving a particular problem, can put up blinders. “If you want to be a successful entrepreneur because you want to prove all the people wrong who didn’t believe in you, then you won’t always have a clear view of what needs to be done in a particular moment,” says Anhalt. “I’ve seen founders who didn’t pivot, even though they needed to, because they were so singularly focused on their original idea and they didn’t allow any room to change or have it look different.” 

As First Round’s Special Partner in Decision Science Annie Duke so aptly put it on the Review, “The hardest thing to quit is who you are.” (Her new book, “Quit: The Power of Knowing When to Walk Away” tackles this touchy subject head-on.) 

How to get to the root of your “why”

This is where it’s critical to set aside the time to dig deeper, away from the constant drumbeat of to-list items. Even if that means a harsh wake-up call. “The truth is, not everyone should be a founder. And there are a lot of people out there who would probably live a more satisfying, meaningful life doing something else. But they feel that it’s the only way to prove to themselves or their family or the world that they’re valuable, successful, and worthy,” says Anhalt. 

How do you know if you’re in it for the “right reasons” (to borrow a popular phrase from reality dating shows)? ”She suggests putting pen to paper as you reflect on these questions:

If this company doesn't have a "successful" exit, will I still be glad I spent my time on it?

Do I get satisfaction from the change we're making along the way (versus only looking ahead to the goal of an exit)?

When I look back at these years of my life, will I feel proud and excited about the work I was doing?

Partnering with a therapist or a coach can also start to peel back the layers. “When I work with founders, I tell them directly that my goal is not to make sure that they have the most successful company possible. My goal is to help them feel like they’re satisfied and happy about the life they’re living — because we only get one,” says Anhalt. “Is your ultimate goal proving something to the world? Or is the ultimate goal being successful at finding product-market fit and solving a problem that you’re passionate about?”

Because if your driving force in starting a company is to fill a void deep within yourself, Anhalt warns that you’re setting yourself up for disappointment. 

The great myth of entrepreneurship is that the founder’s path will get you all the autonomy, validation and recognition that you’re craving. It won’t — definitely not right away, and often not at all. 

“I can’t tell you how many founders I’ve worked with who finally reached the place that they were so sure would make them feel competent, successful and satisfied. But that milestone comes and goes and it doesn’t bring fulfillment — and it’s crushing, because they work so long and hard to get to that place,” says Anhalt.

In addition to working with a trusted professional to help unpack the deeper layers of yourself, Anhalt returns to a common prescription across these traits — make the time for other pursuits that bring you joy and fulfillment, whether it’s challenging yourself in a workout class, cooking up a new recipe, or going for a walk with a friend.

WRAPPING UP: CARE FOR YOURSELF LIKE AN OLYMPIC ATHLETE

Still unconvinced that you need to take care of your own emotional fitness as a founder? To make one last pitch, Anhalt leans on one of her favorite metaphors. “The comparison that I’ve given before is that of the Olympic athlete. If you look at what they do to their body, in service of being the best, it’s not actually the healthiest lifestyle to train that hard for that long. Look at how many serious injuries athletes face because of how hard they work,” she says. “Similarly, I wouldn’t say that being a founder is the healthiest version of having a balanced life. There are incredible levels of stress.”

When you put your physical and mental health through a gauntlet, you’ve got to give it some extra TLC. “I have founders say to me all the time that they’d like to try therapy or coaching, but they’re too busy running a company,” says Anhalt. 

Can you imagine if an Olympic athlete ate fast food every day because they said they were too busy to nourish their bodies with healthy food? How the hell are you going to win gold on fast food?

You will never be able to achieve the extraordinary without proper fuel, support and rest. So if you haven’t already, book time with a founder coach or therapist (or both!) to hold you accountable to your goals — dialing up your strengths deep within your founder DNA, while dialing down the weaknesses that might be sneakily holding you back.

Photography by Bonnie Rae Mills / Illustrations by Karyssa Heine