Turning disappointment into positivity as a Portfolio Executive

A man looking wistfully out of a window with blinds casting shadows on his face

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One of the toughest things to deal with when you are setting out as a Portfolio Executive is disappointment. You may have felt less sensitive to it when you were in your previous corporate life because you could always tell yourself that the ‘no’ wasn’t really about you – it was because of the organisation. Or perhaps you weren’t directly involved in sales in your former role, so it felt less personal. But when it’s you, as a solo Portfolio Executive, there’s no such option. And you don’t have the benefit of a team around you to lift your spirits either.

The disappointment we feel when it’s our own show is much stronger and that’s inevitable. We put all our energies and ideas on the line, so hearing ‘no’ or ‘maybe next year’ can hurt. We have prospects we are convinced will become our next client, but they don’t happen. And even when we think all is well with a client who has said ‘yes’, the situation can change.

Your new business and workstyle are just too important to let disappointment harm your progress, so you need to develop a way of dealing with it.

So this article is about dealing with the inevitable disappointment you are going to experience. I’ve spoken to many people who’ve made the transition from corporate life to the independence of a Portfolio Executive role, often as they enter the 2nd half of their careers. As we reflected we often found the positives from those disappointing outcomes.

Here are my tips to help you do that – and come out of the experience more positive and resilient.

1: Develop a habit of gratitude

There is a really interesting phrase “if you want to maintain your appointment, then do not allow yourself to be dis-appointed”. It is so easy to allow your disappointment to actually rule you out of the running, to take you out of position and to undermine what you have already got. The most powerful way of dealing with disappointment is actually to continually have a habit of gratitude. To find the things within your new role and workstyle to be grateful for – and there will be many.

You’ll probably feel less stress, more control and freedom. Perhaps it’s the opportunity to spend more time with your family, to improve that work-life balance that you’ve struggled with for so long. Build the habit of being grateful for every day. Find something to be grateful for in your business, your relationships, yourself, the opportunities you find, the kindness of others, success, extraordinary luck/provision that you have experienced.

If you can get in the habit of every day finding the things that you can be grateful for then when you are disappointed, it will just be a little blip. Building an attitude of gratitude is the most powerful way to inoculate yourself against disappointment.

2: Don’t stress over the numbers

I had a really interesting conversation with one of the people who I am helping to build a portfolio executive role. His background was corporate finance and he was getting quite distressed that he was not closing enough deals. We had not been working together for very long and I asked him when he was in corporate finance what proportion of the deals actually closed. And he said about 1 in 10. In other words 9 out of 10 of those opportunities failed to close.

So why was he surprised that out of the last five deals we had talked about, none of them had closed? Things could have got off to a better start, but he wasn’t doing any worse. It just felt worse because it was more personal.

3: Look at disappointment as a learning opportunity

Don’t just brush off the things that have not worked: take away some valuable lessons. One of the best ways of turning disappointment into something that gives you growth, is to look at how you could learn from the experience.

Here are three questions that I always ask about learning.

  • What could I have done differently? Sometimes the answer, frankly, is nothing. That is a perfectly good answer, but think a little deeper and try to see it from the next two perspectives…
  • How could I have been different in this? What is the different person that I could have shown up with? Whether an attitude, a skill, a knowledge or an experience. How could I have been different?
  • How else could this have panned out? We are in the world of opportunity and risk, and opportunities have a certain likelihood of happening or not happening. And risks have a certain likelihood of occurring or not occurring. So, look at the other possibilities because at some point you made a rational decision to go down a path that led to either a disappointing outcome or a more encouraging outcome, and remind yourself of what the other opportunities were.

Looking at it from a risk perspective will help you calibrate if it was reasonable to take that risk, if it was reasonable to take up the opportunity. And sometimes absolutely it was, sometimes you properly assessed the risk, it was a reasonable risk, it was a risk you could afford to take, and you mitigated the damaged it caused and maximised the opportunity of avoiding it and it was a sensible thing to do. Because the potential upside was big enough (and it just might have come off!).

4: Get the right people around you

The other part of dealing with disappointment is having people around you who can encourage you when things are not going so well, and whom you, in turn, encourage when they are not going so well.  People who can help you shift your perspective so that you look up rather than look down. People who may also tell you very frankly that that was just a stupid thing to do – but don’t do it again because you’re not that stupid!

Having people around you who you can have honest and open conversations with is really important and I would encourage you to find other people who are portfolio executives, who are freelancers or consultants, who understand the world that you are in. They’ll be people who understand this world of working as an independent and will support you through the good times and the bad.

My last Insights post was about the value of a good network, so I’d urge you to read that too as I go into more depth about the types of people you’ll want around you as a Portfolio Executive.

In conclusion

Disappointment will affect all of us at some point in our careers – whether we are self employed or not. However, when we are faced with it while running our own business, that disappointment will, understandably, feel more personal. And yet, many of the positives that come from being in a different workstyle, such as being a Portfolio Executive, are things we can be grateful for. Channelling that gratitude can often put disappointment onto perspective. It may not even be as bad as it may seem if you can step away from the issue, see things differently and learn from the experience.

One of the best ways to counter disappointment is to build a network that will also become your support network. That’s something we encourage as part of our Portfolio Executive programme; more details can be found here.


Charles McLachlan is the founder of FuturePerfect and on a mission to transform the future of work and business. The Portfolio Executive programme is a new initiative to help executives build a sustainable and impactful second-half-career. Creating an alternative future takes imagination, design, organisation and many other thinking skills. Charles is happy to lend them to you.