This weeks topic is as pervasive as it is taboo in entrepreneurship.

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 founder and investor perspectives on this topic, so please leave a comment.

Isolation, depression and being an entrepreneur

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.

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, those building businesses.

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

They rightly admire the tenacity, resilience and conviction of founders and walk away for 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, they 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 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 founder 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 ‘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 (that’s always happening). But outside of their family, founders spend 80 to 100-hour weeks building products, selling and forging partnerships, nurturing teams and managing finance and operations, all in the face of nailing one win for every 50 setbacks.

They are all in. Family, reputation, relationships, capital. Everything. The feeling of responsibility that founders live with to deliver is enormous.

It takes a village to build a business

I’m continuously on the lookout for signs of all-positive-all-the-time answers, the isolation signal, from friends building businesses and my mentees.

I know enough to know it’s naive to think the relationship between isolation and depression is linear but I take this signal of isolation seriously because I’ve seen it as the precursor to depression too many times. I also understand that isolation is relative and dynamic. And not surprisingly, it often correlates to the entrepreneur’s rollercoaster.

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.

Instead of asking ‘how’s everything going?’, 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?

And 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 deliver on the offer.

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

It’s also up to the founder

Most founders have mentors. We’ve made the ask to people that can help 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.

It starts with a simple ask to a person you know can provide value to your thinking, ‘can we connect for 45 minutes each fortnight for the next three months to work through issues and opportunities for my business?’

Not everyone has the time to mentor but many do. Expect this to be a relationship based on the 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 the core

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

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

Next stop, relationship breakdown.

I’ve written about this before and at the centre 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, let alone find a way through it. And at the end of the day, I didn’t want my partner to be burdened with my challenges.

I started this venture.

These were my issues to solve.

I was also convinced that she wouldn’t understand, not because she wasn’t capable or thoughtful, but because she wasn’t in the trenches. How could she possibly understand and even if she did, where would I start?

But she felt the same stress, angst and jubilation that I did. It’s easy to forget that our partners are riding the same rollercoaster as us. 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. And they do all of this with only a fraction of the context and information in our heads.

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

Relationships fail when 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 entrepreneurs 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.

And if your partner is on the ride with you, ask them 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 a conversation, let me know your thoughts below.