A newsletter for high achievers who want to ensure their new business is a success, offering tools for clarity, confidence and focus. From certified coach, Ellen and Founder of The Ask®.

How to get back up again after you fall in entrepreneurship

When you're taking risks, dreaming big and going for gold... you won't always reach the stars. Here's how to pick yourself up again after a fall.

Jul 13

Illustration Credit: Swarnima Jain x The Ask®

We rarely like to admit it openly when it happens, but often things do not go our way in entrepreneurship.

A deal you were excited about fell through…A new sales launch failed... A client fired you… You had to take out yet another loan to cover costs… killed a project you’d had your heart set on

This is par for the course of entrepreneurship and precisely why we are told to master the art of resilience — because there are just so many opportunities to put that resilience into practice. Aren’t we fortunate?!

As is often the case I write this newsletter in response to themes in client sessions or my own journey of running a business and continually striving for bigger and better things. This time around it is predominantly from personal experience that I write, following a recent professional setback. The details of which I will spare for today as some lessons are still being absorbed. However, in the true fashion of this newsletter, you can bet I will share those lessons when the time is right.

So if you too are in need of picking yourself up and dusting yourself off after a fall, this post is for you. Here are the three steps to take after a setback in entrepreneurship.

Take time

When something goes wrong our instinctive reaction as entrepreneurs is often to bounce right back up and take fresh action.

We might even shame ourselves for thinking or feeling negatively, believing that it would waste time to sit around licking our wounds when instead we could be getting back out there and doing it all over again. Very often I have taken this approach and acted as though any wallowing in sorrow was foolish.

Yet lately I am wondering, if all this gung-ho attitude verges on toxic positivity and could be doing me more harm than good.

That’s because as a therapist would tell you, you can’t fight those feelings. So if you feel sad, disappointed or hopeless then those feelings will rarely go away just because of your efforts to remain productive. Rather, you could find those feelings transfer to your business in other ways if you don’t let them out — perhaps resulting in cynicism, apathy or burnout.

This quote from Mark Manson has helped me to explain this concept:

“Everything worthwhile in life is won through surmounting the associated negative experience. Any attempt to escape the negative, to avoid it or quash it or silence it, only backfires. The avoidance of suffering is a form of suffering. The avoidance of struggle is a struggle. The denial of failure is a failure. Hiding what is shameful is itself a form of shame.

Mark Manson, The Subtle Art of Not Giving a Fuck: A Counterintuitive Approach to Living a Good Life

So armed with this newfound insight I now believe that it is better to let this energy sit with you. Feel into those (hard) feelings for as long as that might take. Sure you might not be able to take a week off work — but if you can maybe you should? — but you can you find ways to reduce your contact hours and carve out some alone time to cry, sleep, journal or watch Netflix?

Professional disappointments are rarely something we give cultural credit to as we might do a break up, death or illness.

They are not ‘matters of the heart’ so we can easily dismiss them as trivial. Except… we often DO pour our heart and soul into our work. So when work doesn’t work, it can be painful.

I recall feeling as though I was in mourning when a big project I had poured 18 months into got pulled almost overnight. This was whilst working a job in 2019 and I and ultimately ended up leaving eight months later as the realisation sank in that there was nothing else for me in this organisation.

This recent experience again I certainly felt a loss. A loss of a reality I had painted in my head and worked towards for months on end. As such, being met with this new reality was a period of readjustment so pretending I was ‘A-OK’ about it wasn’t doing me any favours.

Every time I went to do work I came up with many excuses, felt lethargy or distracted and couldn’t face it.

Until I stopped for a bit. Allowed myself to feel and be sad. On a call with a friend I finally admitted ‘This really sucks’ and only then, after some time to heal did I feel ready to put my detective hat on and figure out quite exactly where this had this gone wrong.

Which leads me to step two…

Take stock

Once you’ve recouped your professional losses make sure that you learn from them.

Hindsight is a wonderful thing. So when you get the opportunity to use it, do. With hindsight we get access to seeing the error of our ways; mistakes made along the way and moments of inflection where we made certain choices.

Dig through your memory archives and understand the steps you did (or didn’t) take that led to this ‘fall’.

Did you made decisions in haste? Miss some important data? Neglect to follow your values or own rules? Miscommunicate? Aim too high or too low?

Not every failing is our own, of course, and there may be other factors outside of your control to consider. But entrepreneurs don’t get to play the blame game. Taking personal responsibility is key and the buck always stops with you.

How you choose to ‘take stock’ is entirely up to you. In my case, taking stock has been a slow process that is being pieced together through various means over the space of a few weeks.

For you, it might look like:

Checking in with your vision, mission and values. Were you out of sync?
Reviewing the data from your experience eg. customer conversion rates, email exchanges, documentation of tasks
Competitor analysis and industry trends. Can you learn anything about others in this space and how your business compares?
Comparing this experience to other similar experiences of your past. What did you do the same or differently?
Analysing your successes and your losses- are there patterns to be found? By understanding your own tendencies and where you best perform you’ll be able to rewrite your own set of roles and responsibilities accordingly.

The more specific the better and you will begin piecing things together.

I run my entire business on Notion and so naturally have dedicated multiple Notion pages to this process.

After I finish taking stock I am reviewing multiple parts of this business and this screenshot shows just some of those aspects which I am looking at:

Example of reviews I am now doing in my business

The thing that has made the biggest different to me so far, however, is getting some perspective from others. Step three — perspective.

Take perspective

With the help of other people you get to see your situation differently and reach conclusions you may not have been able to make alone.

Most of the worlds’ greatest performers, athletes and executives have an army of professional support around them. People who make them better physically, emotionally and in their craft.

Running a business is no different — and as great as you are — you can’t do this alone. So get people in your corner to help you to sharpen your thinking, to push you harder and to learn from.

After you fall down, these people can offer a perspective that you can’t see, because they are not you. They don’t feel your pain, anger or shame and with this objectivity comes better insights.

I reached out to a few people I would consider mentors after this recent experience and had some very helpful responses to shift my thinking and do the right next thing. I have also been on the hunt for a new kind of service provider to support me in my business who brings skillsets I don’t have myself.

Experts can give you tools to build yourself back up and they can help you reframe experiences in new ways.

Perspective is also so powerful because the sheer act of verbalising something can relieve us of some of its pain. The expression “A problem shared is a problem halved” in my experience is accurate, and I know for my coaching clients, is precisely why coaching is so powerful.

I’ve lost count of the number of times a client feels better about something after sharing with me, and say, “I’ve just realised this is not such a big issue after all” as they gain clarity through the act of talking.

Talking it out can sometimes be all that you need.

But talking it out with the wrong person (who doesn’t care, understand, or who gives ill-fitting advice) is to be avoided.

Taking perspective requires discernment. Not everyone has the power to help you nor fully understand what you should or can do next, so choose carefully.

Being a coach to people’s professional lives means most of the time, when an issue occurs, I am asking questions. I am not trying to prove my knowledge or creativity, but rather to listen intently. Listening allows you to pick up on cues and patterns, and ask pertinent questions that give the client more insight into their situation.

Part of my coach training was about learning to ask questions that are for the client’s benefit and not questions from a place of self-interest. I may want to ask details that are juicy to satisfy my line of curiosity, but the client needs me to ask the questions that will move them forward and allow them to see themselves more clearly.

Conclusion

No matter how much time, stock or perspective you take after a professional set back, you won’t be able to prevent more from coming.

They are coming because the very nature of going after hard things in life and business means that there is a risk you will not succeed in your pursuit. But you choose this path because the struggle is worth it, right?

Because on the other side of that challenge, lies the reward of knowing you tried.

Shoot for the moon and if you miss you will still be among the stars.

Cheesy line but one worth keeping in mind during your journey. The losses are your battle-scars of entrepreneurship — the proof that you are doing it right.

A lot of what I write about in this newsletter is not the tactical skills required entrepreneurship but the meta-skills of being an entrepreneur. Of having the right attitude, disposition and strength. Of knowing that when you fall you can get back up again.

I have been pleasantly surprised at how I have handled my set back overall and know that is because I have two years of practice now.

So tehe biggest piece of advice I can give in this post is about cultivating resilience. By working on your resilience you will be better equipped to handle these challenging times and professional set backs and the benefits transfer to other areas of your life.

Taking decisive action, using critical thinking skills and asking for help are all good traits for an entrepreneur but also for life.

Entrepreneurship is life’s training ground and teaches you that whilst you are not in control you do get to control your response. Make it a good one!