Working in London I often walk past people sleeping rough. Sometimes I give them money, and sometimes I don’t. I’ve been wondering why that is, and whether giving money is the best thing to do.

When I worked at Chordiant (now Pega) for a while I was up in Glasgow. Flights were from City Airport and the cab driver used to cut through Cable Street. I remember reading an obituary of Bill Fishman who took part in the Battle of Cable Street.

Obituaries give us a story of a person’s life. They also remind us of our own mortality and prompt us to consider the story we’re writing with our own lives. The Stoic philosopher Seneca reminds us that Life is Long, If You Know How To Use It.

I noticed this:

Recalling that his grandfather, a rabbi, never passed a beggar without giving a donation, he said: “I asked him once what if the man was a scrounger or a drug addict? My grandfather said: ‘Let that always be on his conscience, never yours.’ ”

When I ran the London Marathon in 2010 and 2011 the first time I ran for Sentebale, having visited Lesotho in 2009 and seen the problems the country has with AIDS and HIV. In the process of raising sponsorship I had an exchange with a colleague who declined to sponsor me; he felt that not enough would go to the people it’s designed to help. This wasn’t aimed specifically aimed at Sentebale though. Here’s their 2016/17 report accounts.

A friend asked me why I chose to support Sentebale when there were many causes closer to home. Fair point. The second year I split the money between Sentebale and a local charity that supported young homeless adults.

We tend to support causes that are in front of us.

Should we give money directly to the person who may need it? How much? Is it money they need? And assuming we don’t have unlimited funds, how do we prioritise? Do we have enough information to make an informed decision? It’s not straightforward.

Some people get into difficulty through circumstances beyond their control or lack of education. Perhaps they can no longer afford their rising rent. When I was younger I used to believe that you make your own luck. Returning to philosophy, the Stoics remind us that there are things we can control and things we can’t. (Read the Daily Stoic for an introduction.)

If you’re not comfortable giving money to someone on the street what else can you do?

Here are some ideas. These sites are UK-based but the principles apply more broadly, and you can use Google for more local results.

Here are some people already using technology to make a difference.

In the UK:

  • Next Meal - list the nearest charities that provide food and support for homeless people
  • Street Link by Homeless Link - connect people sleeping rough with the local services that can support them. Metro
  • Beam - Help a homeless person to train up and get into work

United States:


Do contact me if you’re involved with helping the homeless, and have insights as to what does work.