Attracting clients who are willing to invest in using a problem structuring method (PSM) can be particularly difficult for the emerging generation of modellers. There are many reasons for this, not least that the benefits of a problem structuring intervention are vague and evidence of benefits are often anecdotal for example, claims of constructing a deeper understanding of the problem or building the commitment of a group to implementing an outcome. This paper contributes to the evaluation of problem structuring methods by reflecting on the quid pro quo that a client and problem structuring modeller can enjoy from collaboration. The paper reflects on 21 cases, where Journey Making (a problem structuring method) was used with 16 organizations to help managers agree a suite of actions to tackle a complex strategic issue. The reflections are clustered around those benefits that pertain to: PSMs in general; PSMs that use computer-supported workshops; the Journey Making methodology.