Isolation, Depression & Being An Entrepreneur

This week’s post is a topic that is as real and catastrophic as it is taboo in entrepreneurship.

A blunt message... 

It’s a blunt message that’s contrary to entrepreneurship’s often upbeat narrative, and while difficult to talk about, I’d like to know your perspective and that of founders and investors so please leave a comment below.

Well-known to some and an unexpected to others, isolation and depression (not just being tired -- but feelings of severe despondency and dejection) don’t affect every founder, but it’s more common than you might think.

Yeah, we talk about it -- do you?

These topics often come up in conversations with my founder friends and mentees because they (and their spouses who are along for the ride) are the operators in building these businesses.

Those who recoil at these seemingly extreme conditions are people on the sidelines. They are observers of a popular culture, one synonymous with t-shirts, jeans, sticker-clad laptops, pitch competitions and product launches.

They rightly admire the tenacity, resilience and conviction of founders and walk away from startup events feeling inspired and craving more of the infectious vibe.

Meanwhile, the operators continue to drive hard in shadows.

While trying to be the best they can for the people they love, the founders are always running out of time to grow their business. They are always trying to learn in the face of compounding fatigue and they are always trying to increase the quality of their decision making.

At the same time, they are under no illusion that they are volunteers.

Founders readily admit that they didn’t expect to have to wage such a sustained campaign to stay in the market long enough to achieve their vision. And the irony isn’t lost on them that everything they have built, everything you see today, is always only a small part of their ambition.

The founder’s struggle is real but it’s not new.

The entrepreneurial pop culture is only a decade old. For generations before this business, women and men faced the same challenges, the same isolation and the same risk of depression.

  Veneer of positivity

Founders are optimists. We know that in just about all circumstances a positive attitude is infectious and shouldn’t be underestimated. It helps us to inspire teams, partners and customers, and see silver linings amid the startup chaos.

But positivity can go too far and here’s the punchline:

The strongest signal of founders' isolation is when every answer to every question asked by everyone - is positive.

This veneer of positivity deflects away from talking about issues. It’s protection from answering even the most innocent of questions.

Take, for example, asking a founder "How’s it all going?"

You might get a brief bullet-point summary of milestones.


An isolated founder will almost certainly think "there’s no point explaining, they won’t get it," and respond with a deflecting, " Hey, it's all good!"

And the context is important.

When you ask a founder a question there is also a very good chance that they’ll be processing a ton of decisions in parallel -- because this is always happening. But outside of their family -- founders spend 80 to 100-hour weeks building products, selling and forging partnerships. They must nurturing teams and managing finance and operations. 

Every single task that is expected of a founder -- is faced in the burning fire -- of nailing one win for every 50 setbacks.

The founder is all in. They have put EVERYTHING on the line. Family, reputation, relationships, capital. Everything. The feeling of responsibility that founders live with is enormous. They MUST deliver.

It takes a village to build a business.

I’m continuously on the lookout for signs of the all-positive-all-the-time answers. Remember that it is the isolation signal from your friends building businesses and from your mentees.

I know enough to know it’s naive to think the relationship between isolation and depression is linear. I take this signal of isolation seriously and you should too.

I’ve seen it as the precursor to depression too many times. I also understand that isolation is relative and dynamic. It is not surprising if you will become aware -- the isolation and depression often correlates to the entrepreneur’s rollercoaster.

What is your radar picking up?

That said, I hope you open your radar to this signal and act differently when it emerges with your founder friends.

Here’s what I do:

Check in regularly with them. Doesn't have to be big -- just check in.

Resist the urge to ask, "How’s everything going?" Instead, ask them about their family or the common ground you share.

Then serve them this:

I know you have a lot on but I want to help you with one issue you’re trying to work through. So, how can I help?

If they cannot provide an answer, follow up with a message a week later letting them know that the offer is still on the table. Then -- this is important -- deliver on your offer.

Isolation is eliminated by meaningful help from people you trust. It’s no more complex than that.

I know -- it's up to the founder.

Most founders have mentors. We’ve asked and made arrangements with these people who can help us, and we speak with them regularly to get help.

If you’re a mentor-less founder, that needs to change. You can’t build a successful business on your own. Maybe physically you can build by yourself -- yes. But, mentally -- no.

It starts with a simple question to a person you know can provide value to your thinking. You ask, "May we connect for 45 minutes every two weeks for the next three months to work through issues and opportunities for my business?"

Not everyone has the time to mentor but many do -- and they WANT to help you. Expect this to be a relationship based on an exchange of value. You might not know how to thank them for their time but if my experience is anything to go by (and female entrepreneurs please explore this), it all comes out in the wash.

Strengthening your core.

Isolation can also be brought home. The nature of the relationship at home with your partner is more intimate. And here I think about isolation differently.

At home, isolation leads to the creation of what’s known as an entrepreneur’s widow(er).

So -- stop relationship breakdown.

I’ve written about this before and at the centrer of the solution is over-communication with your partner.

As a first time founder in 2008 I struggled immensely with communicating the challenges I faced each day in building my company -- to my loved ones -- and in particular my partner.

Some challenges were petty, others were significant and at the end of each long day, exhausted and with traction and capital waning, I often didn’t have the words to describe the current state I was in, let alone find a way to wade through it.

Then -- at the end of the day, I didn’t want my partner to be burdened with my challenges.

What I said to myself was:

"I started this venture.

These were my issues to solve."

I was also convinced that she wouldn’t understand it anyway. Not because she wasn’t capable of thinking this through -- not that she wasn't thoughtful enough to "get it." She was! But my thoughts were that because she wasn’t in the trenches, how could she possibly understand the whole mess? And even if she did -- where would I start to explain?

What I didn't understand from my own puddle of muck was that she was feeling the same stress, angst and jubilation that I was feeling. It’s easy to forget that our partners are riding the same rollercoaster as we are. 

They carry the load when business travel calls, they provide encouragement from the sidelines, and they help pick up the pieces when luck is in short supply. They do all of this with only a fraction of the context and information that we are carrying around in our heads.

By the way, if you’re a founder and thinking-- "thanks, but this isn’t a thing for me," you’re either single or about to become single.

Relationships fail when the information sharing stalls.

In most normal, low-pressure environments over-communicating is the act of repeating the same message ad nauseam.

The context for founders is usually different. They usually under-communicate with their partner. The good news is that over-communicating is straightforward -- but like any disciple takes practice.

And at its core over-communicating means finding common ground to create a shared understanding that will short-circuit angst while further strengthening a relationship.

Start by asking 5 questions

Here are five questions that founder should ask their partner. This isn’t an exhaustive list and not all of them relate to building a company.

1. Can I practice pitch with you?

Founders should always be closing deals with new customers, partners, investors or hires. The safest audience is your partner so give them permission to adopt the character and pitch them.

2. Can I get your thoughts on this value proposition?

If you’re spinning your wheels on developing messaging for a new feature or product, ask your partner for their input and how they would describe it to a friend over coffee.

3. Can you play with this new version of our product?

This is an easy one and it’s all about observing and capturing how your partner engages with the product. Try also asking what it would take for your partner to share your product with everyone she knows.

4. Do you have any thoughts on how to manage (insert tricky situation)?

Entrepreneurship is like fire-fighting. There is always a spot fire to extinguish and a tricky situation to manage. Ask your partner’s opinion about how they would handle the tricky situation at hand.

5. How can I help?

This is probably THE most important question that a founder should ask their partner each week, if not each day. This question is a surefire way to reconnect and put your money where your mouth is in terms of being mindful and engaged in your relationship.

Closing thoughts

- If you know someone building a business and they’re being too positive, act.

- If you don’t have mentors and you’re building a business, change that.

- If your partner is on the ride with you, OR NOT, ask them the five questions.


Just don’t ignore it. Being isolated is a sad existence which can lead to a devastating outcome.

*Consider this the start of your conversation, let me know your thoughts by leaving a comment.