When to quit as an entrepreneur and business owner in Singapore

Recently, I was speaking to my therapist.

I don’t know if this is the right thing to do…

You know, it feels like everything isn’t working…. Right?

Right now, it feels like everything is falling apart.

My therapist smiles.

He says to me,

John, do you realise how many times you used the word ‘right’?

Maybe there’s no right or wrong thing.

Maybe the better question to ask is:

“Is it working right now or not?”

It struck me. That night, I was ready to drop it as an entrepreneur.

After all, for all the efforts I had made, I had earned a paltry $113.

That’s right.

Not a million, or even a thousand, but a 3-digit sum.

Was this the right thing to do?

As an entrepreneur, you’re struggling with a great deal of uncertainty. You wonder when the next gig is going to come, or whether people are going to buy your product.

Today’s article hopes to share some principles you can use in your journey. Take it as one struggling entrepreneur to another. Not a ‘business guru’ to another…but a heart to heart talk between two people who are struggling to pay themselves.

Uncertainty is a lifelong thing.

I asked an entrepreneur recently. He had been doing business for 20 years. By all accounts, it seemed like he was doing well.

How do you keep going? Don’t you ever think of quitting?

He laughed.

Yes, I think of it everyday!

I laughed.

Entrepreneurship, for all the snazzy attention that Silicon Valley has about making the next tech darling, is a very scary thing.

As Shane Melaugh, the founder of Thrive Themes shared, being an entrepreneur is like being a sailor in an open sea.

You are buffeted by waves… at every turn.

The trick isn’t to wait for calm seas.

But the trick is to learn to be a better sailor.

The tendency for us is to think that once we get to $X a month, we would have made it. We are on the hedonic treadmill where we say,

If only… if only I could have X customers a month…

If only I could have X revenue per month…

If only if only. If only-s end up building a place where you are never enjoying where you are, at this moment.

Enjoying the uncertainty.

Why did you get into this in the first place, if you wanted certainty?

You could get a job, clock in, clock out, and have a steady paycheck at the end of the month, isn’t it?

You wouldn’t have to work so hard. But let me guess, part of you enjoys that uncertainty. Of not knowing what’s next.

You want to create your way through that, rather than wait for someone to tell you what’s the way through it.

As a client once told me,

You grow through what you go through.

The principle with uncertainty is to first accept that it will be a lifelong struggle as an entrepreneur, even when you are earning billions per year.

The principle is to look at the uncertainty as a crucible to hone your skill.

Look at it as skill building.

I admit.

I run a business that focuses on training young people.

For all the pitches I have made about training people, I have only managed to get…

Zero.

Zero invitations to train others.

That might be your experience.

You are sending email after email, pitch after pitch, ad after ad… and you are wondering how you’re ever going to sell your darling.

Remember when my therapist said there’s no right or wrong thing? Only whether it’s working now or not?

Use that feedback to calibrate your approach to getting business. This might be different for each business you’re in.

The first thing to do is to understand where your specific value-added skills are.

For example, you might be a writer. Your specific value-added skill is in writing stories, and helping people to bring out the power of those stories.

You enable stories to land powerfully with people. You help people to feel.

Now… you may not be getting paid right now for that writing you do.

Your work is not getting published in major printing houses.

The second aspect is to get stuck in the do-loop, not the doom loop.

Eric Ries, the author of Lean Startup, instructs people to build, measure, learn. Go on the active learning cycle.

You only learn as much as you do.

So do, adjust, and do again.

Step off the doom loop of self-doubt, self-defeat, and self-flagellation.

Symptom 1 of the entrepreneur?

Self-doubt. You question if you’re doing the right thing. That then evolves into self-defeat.

You wonder if there’s any point doing anything!

Then that becomes self-flagellation. You beat yourself up for doing nothing.

Step off the doom loop.

It does nothing for your mental state.

I confess.

In recent times, I have been on that doom loop. I sit down at my laptop, stare into the screen, and go all over the internet.

When I see an opportunity, I think to myself,

Oh there’s no point. I’m going to fail anyway. No one is going to want my services.

Then at night, after a long day of scrolling, I look at myself and say,

What a weakling! You didn’t do anything today!

I do everything but the thing that will get me more business – pitching for business.

As cliche as this sounds, be kind to yourself.

There are going to be days like this.

But ask yourself:

What is my bottom line?

This concept, adopted from family therapist Virginia Satir, speaks inherently about the line you won’t bulge on.

For me, it is:

No matter what happens, come hell or high water, I will never give up.

I will do everything within my control to build a place where young people are comfortable with talking about their emotions in a safe way.

How about you?

What is the thing you will never give up on?

What is your vision? Why are you doing this?

Then you start tracking your actions. It can be simple.

For me, it’s building a list of leads on Microsoft Excel. I then make a promise to myself that I will make sure that list grows.

What about you? How are you tracking your baseline performance, so that you can ensure that it grows over time?

Then you celebrate yourself.

With so much uncertainty, your first duty is to take care of yourself, so that you can go out and sail your best each day.

I have taken to writing a love letter to myself everyday.

For example, I write down how I’ve progressed that day, and the specific examples I have shown of progress.

This keeps you focused on progress, rather than perfection.

Don’t fight alone

Entrepreneurship is one of the hardest jobs out there.

For all the glitz and glamour of ‘doing your own thing’, being your own boss, and owning the world, it’s much more than that.

It’s a place of deep self-doubt, fear, and uncertainty.

It’s not about hoping for the load to be lifted off your shoulders.

It’s hoping, and building, stronger shoulders, and more importantly, about building together with others.

Early in my journey, I realised that I couldn’t do this alone, and I really needed someone else to help me. Even when I was starting out a content agency, I was constantly looking for partners. My ex-business partner used to think I was crazy. He would say something to the effect of,

John, you can do this alone and make 115k yourself. Why not?

My partner saw that he could do it alone. But I couldn’t. I was just not wired like he was.

I knew that part of it was about stoking my ego, and ‘having a team’.

So when I found Jason during a networking event, it was him who helped me to see,

hey John, you can do websites and content so well. Why not just do that, instead of this training thing?

He was one of the earliest sources of encouragement. He would take me to an occasional buffet treat, just to shoot the wind, and enjoy the time as buddies. Nothing more, nothing less, just buddies enjoying a nice meal.

Eventually when I moved to a full design agency doing annual reports and publishing books, again, I realized that I could not do it alone. I kept trying to find long-term assistants who wouldn’t abandon me when the work got too tough.

That was how I later found Stella, who was based in Indonesia, who helped me with my admin and accounting.

I’ve since kept growing and growing the team, but it’s not escaped my consciousness that I’ve only been able to do it because others have helped me.

Business isn’t something you do alone. It’s ultimately to serve other staff, and your customers. Not yourself.

And if you find yourself just serving yourself, then that isn’t a business. You’re just freelancing.