Can founders have it all?

Is the choice between a balanced lifestyle and financial success real or imaginary?

A subscriber emailed me to ask a question I hear on a regular basis from founders:

Is there a way to run a financially successful business while at the same time, staying connected with what's important to us?

Is is possible to take long walks in the morning, stay present with our loved ones, and dedicate time to your favourite hobby, while running your business successfully?

In this essay, I argue that yes, it’s possible, but subject to a couple of important caveats.

Is financial success the only thing that matters?

On the one hand, founders tend to be motivated by creating meaningful wealth. They are also in a unique position to do so. Regardless of how much you excel in almost all professions, you won’t generate significant wealth. Entrepreneurs, if successful, can generate potentially unlimited wealth.

A separate essay needs to be written on how the pursuit of money can be counterproductive if it masks our need for love, safety, and belonging. Jerry Colonna brilliantly explores this topic in Reboot: Leadership and the Art of Growing Up. If we feel unsafe or unloved, deep inside, a billion quid isn’t going to fix that.

But it doesn’t have to be this way. Money can also play a positive role as an enabler of many other things. Dr. Gena Gorlin, a founder coach, just wrote an excellent essay on this very topic.

Yet, on the other hand, money isn’t everything. As my subscriber said, we also want to stay present with our loved ones, have our hobbies and take long walks in the morning (I’m a fan of this myself!).

The early days are always hard

I remember my own experience of starting Makers in 2013. I had never worked harder, either before or since, in my life than I did that year, purely to get the company from an idea to a “default alive” state. I remember days when my alarm would go off at 6 am, so that I could be in the office by 7 am, so that I could put in 16 hours of work and get a cab home at 11 pm, so that I could be asleep by midnight.

I’m not alone in remembering such an experience. Amy Golding, an experienced growth CEO, puts it well in a raw and honest blog post about being the youngest female CEO of a £100m company:

But I can’t imagine there are many CEOs or self-made millionaires out there, who started with nothing, and managed to get to where they are working 3 days a week. The fact is, it’s both. Because as productive as I am, as “smart” as I try and work - I’ll wager I can still get more shit done in 15 productive hours than anyone can in 6. The sun still rises at the same time. There is still the same number of hours in the day. And I will spend more of them working than most people will.

Paul Graham, founder of YCombinator, makes the same point:

Running a startup is not like having a job or being a student, because it never stops. This is so foreign to most people's experience that they don't get it till it happens.

I think of two of my clients, who also happen to be female CEOs. They operate like machines year after year, aiming to both outsmart and outwork the competition. They’re making good progress and are aware that their lives are deliberately skewed towards work at this point.

So, is it impossible, then? Can we not have long, relaxed walks in the morning and run a financially successful company?

The answer to this question depends on two important variables: timing and the desired level of financial success.

The timing factor

Let’s start with timing. As much as I would love it to be the case, I can’t think of many examples of people who started without significant privilege in life and built a successful business through a part-time effort.

Creating something from nothing requires a lot of work, on top of any luck you’ll need along the way. If you bring significant privilege to the table (e.g. your parents gave you considerable wealth, paid for a world-class education and made helpful introductions), it’ll be much easier for you to build a startup more sustainably.

Likewise, if it’s your second or third startup. You’ve already got money, experience, reputation and connections that will make your life considerably easier.

Most people, especially first-time founders, will need to make a herculean effort of the kind Amy Golding describes above.

However, the good news is that it’s temporary. It doesn’t have to last forever. Once the company reaches a certain level of success (being “default alive”), it becomes up to the founder to choose how hard to press forward.

I know several founders who reached this stage and decided that building a unicorn just isn’t worth it. They have a stable, profitable mid-size business and decent savings. They could have chosen to raise the stakes and fight for more, but they chose to spend time walking their kid to school most days and have time for hobbies.

Photo by Jessica Rockowitz on Unsplash

So, timing matters. Having a decent work-life balance and starting a startup are hard to combine. You must be either very privileged or lucky to pull it off. But frontloading your efforts so that you can enjoy the results later is a valid strategy.

Desired level of wealth

Another important variable is the desired level of financial success. The truth is that having a simple and enjoyable lifestyle isn’t that expensive. Long walks in the morning are free, and meaningful conversations with family are free. Sitting quietly and feeling calm and content inside is also free.

What is your idea of staying connected to what’s important to you? What does it mean to live a good life? Does it need an insane amount of money?

Our real needs are food, shelter, and companionship. If we have somewhere to sleep, something to eat, and nice people to share our lives with, we’ve got our needs covered. If we’re healthy, too, we’re already doing better than most people on this planet.

Everything on top is wants, not needs. You choose what level of wants is right for you. For someone, it’ll be a business generating £100k in profits a year. For someone else, it'll be a million. For yet another person, £10 million or more.

It’s generally easier to build a smaller business than a large business. In my experience, many founders, especially first-time founders, underestimate this point. They want to be the “next Facebook” and “disrupt the industry.”

There's nothing wrong with that as long as you understand the chances of success. If you’d rather have a smaller business generating reliable profits, it may be easier to bootstrap something boring like a recruitment agency than build and exit a VC-backed unicorn.

So, can founders have it all?

Well, maybe not always. The initial stages of taking something off the ground, be it a truly innovative business or a chain of restaurants, will be hard for most people in most cases.

However, if successful, you’ll have the option of choosing your lifestyle. If you want to take a £10m company to £100m, it’ll probably require the same focus and effort you put in when you first started it.

Achieving your target level of financial ambition is easier if it is relatively modest. Fortunately, things that matter in life tend to be cheap or free. It’s the toys we don’t need that are expensive.

So, if you’ve got relatively modest needs (which may still look like lots of money to most people) and are willing to work hard for a while to enjoy success later, you can have it all: running a financially successful business and being able to focus on your other interests in life.