How to draw a shape on the entire height of a minipage?

Question

My purpose is to create a nice resume with the arrows indicating the timeline of my experiences. The left column contains information that is not relevant here.

I have the following code:

\documentclass[a4paper,12pt]{article}%minimal working example
\usepackage[french]{babel}

\usepackage{fontspec}%déjà chargé par luatextra
\defaultfontfeatures{Ligatures=TeX} % to have the automatics ligatures of TeX
\setromanfont{Verdana}

\usepackage{paracol} %%Pour les colonnes sur plusieurs pages

\usepackage{multido}

\begin{document}

\setlength{\parindent}{0em}
\setlength{\parskip}{0.5em}

\columnratio{0.32}
\begin{paracol}{2}
\begin{leftcolumn}
Left column

\multido{\i=2+1}{30}{bla ble bli\\}

\end{leftcolumn}%
\begin{rightcolumn}%

\textbf{A title for something that is a little bit verbose}

{\scriptsize a comment about it}

\hspace{2em}
\begin{minipage}{0.6\columnwidth}

\begin{itemize}
\item {\footnotesize bla bla bla}
\end{itemize}
{\footnotesize bla bla again}

{\footnotesize bla}

{\footnotesize bla}

\begin{itemize}
\item {\footnotesize bla bla}
\end{itemize}
\end{minipage}
\begin{minipage}{0.28\columnwidth}
{\fbox{Some stuff}}\end{minipage}

\textbf{A second title  that is a little bit verbose}

{\scriptsize a comment about it}

\hspace{2em}
\begin{minipage}{0.6\columnwidth}

\begin{itemize}
\item {bla bla bla}
\end{itemize}
{\footnotesize one thing}

{\footnotesize another one}

{\footnotesize a third one}

{\footnotesize a fourth one}

\begin{itemize}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\end{itemize}
{\footnotesize something else}

{\footnotesize a last thing}
\end{minipage}
\begin{minipage}{0.28\columnwidth}
{\fbox{Some stuff}}
\end{minipage}

\textbf{Another title}

{\scriptsize etc}
\end{rightcolumn}
\end{paracol}
\end{document}

I would like to add to the pdf output the red shapes as drawn into this example:

The shape should be an arrow as shown there (not necessarily red, I will probably change the color), and will be a vector graphic programmatically drawn. Possibly, I would like it to be filled with a background color.

I want the arrow's height to be constrained to the minipage's height (something like arrow's height = minipage's height - 4em).

I use minipage here because I also draw rounded boxes (the ones with "Some stuff") and have intermediate titles. I give here a minimalist example of what I wish.

I would also like (if possible) that may arrow can be continued when a page break occurs (but I don't know if it is possible using minipage)

How can I achieve this ?

EDIT: here is an exemple of what I would like to do (the left rounded box's height depends on its content, not on the minipage's height)

Answer 1

One possibility using tcolorbox.

Improved version

This improved version admits page breaks as required. I suppressed your minipages and now the original settings (two minipages) as well as the arrow and the "Some stuff" framed box are produced using a single tcolorbox called myarrow; this, in principle, allows for page breaks, but then it's not clear what would happen with the framed box to the right. The syntax is

\begin{myarrow}[<options for the arrow>]{<text>}
contents
\end{myarrow}

where <options for the arrow> can be used to change the attributes for the arrow (see orange arrow in the example below) and <text> is the text that will be placed centered, framed and to the right.

\documentclass[a4paper,12pt]{article}
\usepackage[french]{babel}
\usepackage{fontspec}%déjà chargé par luatextra
\defaultfontfeatures{Ligatures=TeX} % to have the automatics ligatures of TeX
\setromanfont{Verdana}
\usepackage{paracol} %%Pour les colonnes sur plusieurs pages
\usepackage{multido}
\usepackage[many]{tcolorbox}

% Colors for the arrow
\colorlet{arrowbgcolor}{cyan!20}
\colorlet{arrowbordercolor}{cyan}
% Colors for the framed box to the right
\definecolor{boxbgcolor}{RGB}{232,220,236}
\definecolor{boxbordercolor}{RGB}{157,125,169}

\newtcolorbox{myarrow}[2][]{
  breakable,
  enhanced,
  boxrule=0pt,
  arc=0pt,
  frame code={},
  colback=white,
  overlay unbroken={
    \draw[arrowbordercolor,fill=arrowbgcolor,#1]
      ([xshift=0pt]frame.north west) --
      ([xshift=20pt]frame.north west) --
      ([xshift=20pt,yshift=10pt]frame.south west) --
      ([xshift=10pt,yshift=5pt]frame.south west) --
      ([yshift=10pt]frame.south west) -- cycle;
    \node[
      draw=boxbordercolor,
      text width=.28\columnwidth,
      anchor=west,
      line width=1pt,
      rounded corners=10pt,
      fill=boxbgcolor,
    ] at ([xshift=.02\columnwidth]frame.east) {#2};  
  },
  overlay first={
    \draw[arrowbordercolor,fill=arrowbgcolor,#1]
      ([xshift=0pt]frame.north west) --
      ([xshift=20pt]frame.north west) --
      ([xshift=20pt]frame.south west) --
      (frame.south west) -- cycle;
    \node[
      draw=boxbordercolor,
      text width=.28\columnwidth,
      anchor=west,
      line width=1pt,
      rounded corners=10pt,
      fill=boxbgcolor,
    ] at ([xshift=.02\columnwidth]frame.east) {#2};  
  },
  overlay middle={
    \draw[arrowbordercolor,fill=arrowbgcolor,#1]
      ([xshift=0pt]frame.north west) --
      ([xshift=20pt]frame.north west) --
      ([xshift=20pt]frame.south west) --
      (frame.south west) -- cycle;
    \node[
      draw=boxbordercolor,
      text width=.28\columnwidth,
      anchor=west,
      line width=1pt,
      rounded corners=10pt,
      fill=boxbgcolor,
    ] at ([xshift=.02\columnwidth]frame.east) {#2};  
  },
  overlay last={
    \draw[arrowbordercolor,fill=arrowbgcolor,#1]
      ([xshift=0pt]frame.north west) --
      ([xshift=20pt]frame.north west) --
      ([xshift=20pt,yshift=10pt]frame.south west) --
      ([xshift=10pt,yshift=5pt]frame.south west) --
      ([yshift=10pt]frame.south west) -- cycle;
    \node[
      draw=boxbordercolor,
      text width=.28\columnwidth,
      anchor=west,
      line width=1pt,
      rounded corners=10pt,
      fill=boxbgcolor,
    ] at ([xshift=.02\columnwidth]frame.east) {#2};  
  },
  extrude left by=1em,
  enlarge left by=2em,
  width=0.6\columnwidth+1.5em,
}

\begin{document}

\setlength{\parindent}{0em}
\setlength{\parskip}{0.5em}

\columnratio{0.32}
\begin{paracol}{2}
\begin{leftcolumn}
Left column
\multido{\i=2+1}{30}{bla ble bli\\}
\end{leftcolumn}%
\begin{rightcolumn}%
\textbf{A title for something that is a little bit verbose}

{\scriptsize a comment about it}

\begin{myarrow}{Some stuff\\Some stuff\\Some stuff}
\begin{itemize}
\item {\footnotesize bla bla bla}
\end{itemize}
{\footnotesize bla bla again}

{\footnotesize bla}

{\footnotesize bla}

\begin{itemize}
\item {\footnotesize bla bla}
\end{itemize}
\end{myarrow}

\textbf{A second title  that is a little bit verbose}

{\scriptsize a comment about it}

\begin{myarrow}{Some stuff\\Some stuff\\Some stuff\\Some stuff}
\begin{itemize}
\item {bla bla bla}
\end{itemize}
{\footnotesize one thing}

{\footnotesize another one}

{\footnotesize a third one}

{\footnotesize a fourth one}

\begin{itemize}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\end{itemize}
{\footnotesize something else}

{\footnotesize a last thing}
\end{myarrow}
\end{rightcolumn}
\end{paracol}

\end{document}

First version

In this version the desired decoration is actually a freelance design for a tcolorbox. Take into account that since you are using minipages, page breaks are not allowed.

\documentclass[a4paper,12pt]{article}
\usepackage[french]{babel}
\usepackage{fontspec}%déjà chargé par luatextra
\defaultfontfeatures{Ligatures=TeX} % to have the automatics ligatures of TeX
\setromanfont{Verdana}
\usepackage{paracol} %%Pour les colonnes sur plusieurs pages
\usepackage{multido}
\usepackage[many]{tcolorbox}

\newtcolorbox{myarrow}[1][]{
  breakable,
  freelance,
  boxrule=0pt,
  frame code={},
  colback=white,
  overlay={
    \draw[cyan,fill=cyan!20]
      ([xshift=-20pt]frame.north west) --
      (frame.north west) --
      ([yshift=10pt]frame.south west) --
      ([xshift=-10pt,yshift=5pt]frame.south west) --
      ([xshift=-20pt,yshift=10pt]frame.south west) -- cycle;
  }
}

\begin{document}

\setlength{\parindent}{0em}
\setlength{\parskip}{0.5em}

\columnratio{0.32}
\begin{paracol}{2}
\begin{leftcolumn}
Left column
\multido{\i=2+1}{30}{bla ble bli\\}
\end{leftcolumn}%
\begin{rightcolumn}%
\textbf{A title for something that is a little bit verbose}

{\scriptsize a comment about it}

\hspace{2em}
\begin{minipage}{0.6\columnwidth}
\begin{myarrow}
\begin{itemize}
\item {\footnotesize bla bla bla}
\end{itemize}
{\footnotesize bla bla again}

{\footnotesize bla}

{\footnotesize bla}

\begin{itemize}
\item {\footnotesize bla bla}
\end{itemize}
\end{myarrow}
\end{minipage}%
\begin{minipage}{0.28\columnwidth}
{\fbox{Some stuff}}\end{minipage}

\textbf{A second title  that is a little bit verbose}

{\scriptsize a comment about it}

\hspace{2em}
\begin{minipage}{0.6\columnwidth}
\begin{myarrow}
\begin{itemize}
\item {bla bla bla}
\end{itemize}
{\footnotesize one thing}

{\footnotesize another one}

{\footnotesize a third one}

{\footnotesize a fourth one}

\begin{itemize}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\end{itemize}
{\footnotesize something else}

{\footnotesize a last thing}
\end{myarrow}
\end{minipage}
\begin{minipage}{0.28\columnwidth}
{\fbox{Some stuff}}
\end{minipage}

\end{rightcolumn}
\end{paracol}
\end{document}

Answer 2

With tikzmark:

\documentclass[a4paper,12pt]{article}%minimal working example
\usepackage[french]{babel}

%\usepackage{fontspec}%déjà chargé par luatextra
%\defaultfontfeatures{Ligatures=TeX} % to have the automatics ligatures of TeX
%\setromanfont{Verdana}

\usepackage{paracol} %%Pour les colonnes sur plusieurs pages

\usepackage{multido}

\usepackage{tikz}
\usetikzlibrary{arrows.meta}
\newcommand\tikzmark[1]{%
\tikz[remember picture,baseline=(#1.base)]
\node[inner sep=0,outer sep=3pt] (#1) {};%
}
\newcommand\myarrow[3][]{%
  \begin{tikzpicture}[overlay,remember picture]
    \draw[#1] (#2) to (#3);
  \end{tikzpicture}}

\begin{document}

\setlength{\parindent}{0em}
\setlength{\parskip}{0.5em}

\columnratio{0.32}
\begin{paracol}{2}
\begin{leftcolumn}
Left column

\multido{\i=2+1}{30}{bla ble bli\\}

\end{leftcolumn}%
\begin{rightcolumn}%

\textbf{A title for something that is a little bit verbose}

\tikzmark{a}{\scriptsize a comment about it}
\hspace{2em}
\begin{minipage}[t]{0.6\columnwidth}

\begin{itemize}
\item {\footnotesize bla bla bla}
\end{itemize}
{\footnotesize bla bla again}

{\footnotesize bla}

{\footnotesize bla}

\begin{itemize}
\item \tikzmark{b}{\footnotesize bla bla}
\end{itemize}

\myarrow[-latex, draw=magenta!55, line width=5]{a}{a|-b}
\end{minipage}%
\begin{minipage}{0.28\columnwidth}
{\fbox{Some stuff}}\end{minipage}

\textbf{A second title  that is a little bit verbose}

\tikzmark{a}{\scriptsize a comment about it}

\hspace{2em}
\begin{minipage}{0.6\columnwidth}

\begin{itemize}
\item {bla bla bla}
\end{itemize}
{\footnotesize one thing}

{\footnotesize another one}

{\footnotesize a third one}

{\footnotesize a fourth one}

\begin{itemize}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\end{itemize}
{\footnotesize something else}

\tikzmark{b}{\footnotesize a last thing}
\end{minipage}
\begin{minipage}{0.28\columnwidth}
{\fbox{Some stuff}}
\myarrow[-latex, draw=green!55, line width=5]{a}{a|-b}
\end{minipage}

\textbf{Another title}

{\scriptsize etc}
\end{rightcolumn}
\end{paracol}
\end{document}

Another variant:

\documentclass[a4paper,12pt]{article}%minimal working example
\usepackage[french]{babel}

%\usepackage{fontspec}%déjà chargé par luatextra
%\defaultfontfeatures{Ligatures=TeX} % to have the automatics ligatures of TeX
%\setromanfont{Verdana}

\usepackage{paracol} %%Pour les colonnes sur plusieurs pages

\usepackage{multido}

\usepackage{tikz}
\usetikzlibrary{arrows.meta}
\newcommand\tikzmark[1]{%
\tikz[remember picture,baseline=(#1.base)]
\node[inner sep=0,outer sep=3pt] (#1) {};%
}
\newcommand\myarrow[3][]{%
  \begin{tikzpicture}[overlay,remember picture]
    \draw[fill=orange!30,#1] ([xshift=-1em]#2.south) -- ([xshift=-1em,yshift=1ex]#3.north) -- (#3.north) -- ([xshift=1em,yshift=1ex]#3.north)  -- ([xshift=1em]#2.south)--cycle;
  \end{tikzpicture}}

\begin{document}

\setlength{\parindent}{0em}
\setlength{\parskip}{0.5em}

\columnratio{0.32}
\begin{paracol}{2}
\begin{leftcolumn}
Left column

\multido{\i=2+1}{30}{bla ble bli\\}

\end{leftcolumn}%
\begin{rightcolumn}%

\textbf{A title for something that is a little bit verbose}

\tikzmark{a}{\scriptsize a comment about it}
\hspace{2em}
\begin{minipage}[t]{0.6\columnwidth}

\begin{itemize}
\item {\footnotesize bla bla bla}
\end{itemize}
{\footnotesize bla bla again}

{\footnotesize bla}

{\footnotesize bla}

\begin{itemize}
\item \tikzmark{b}{\footnotesize bla bla}
\end{itemize}

\myarrow[draw=magenta!55]{a}{a|-b}
\end{minipage}%
\begin{minipage}{0.28\columnwidth}
{\fbox{Some stuff}}\end{minipage}

\textbf{A second title  that is a little bit verbose}

\tikzmark{a}{\scriptsize a comment about it}

\hspace{2em}
\begin{minipage}{0.6\columnwidth}

\begin{itemize}
\item {bla bla bla}
\end{itemize}
{\footnotesize one thing}

{\footnotesize another one}

{\footnotesize a third one}

{\footnotesize a fourth one}

\begin{itemize}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\end{itemize}
{\footnotesize something else}

\tikzmark{b}{\footnotesize a last thing}
\end{minipage}
\begin{minipage}{0.28\columnwidth}
{\fbox{Some stuff}}
\myarrow[draw=green!55]{a}{a|-b}
\end{minipage}

\textbf{Another title}

{\scriptsize etc}
\end{rightcolumn}
\end{paracol}
\end{document}

Further beautifications like choosing an appropriate arrow, and placing the first mark at suitable place may be done as per your taste.

Answer 3

The following example defines environment timepage that catches the former minipage inside a box for measurement. Then the minipage is placed and the time arrow is drawn via TikZ:

\documentclass[a4paper,12pt]{article}%minimal working example
\usepackage[french]{babel}

\usepackage{fontspec}%déjà chargé par luatextra
\defaultfontfeatures{Ligatures=TeX} % to have the automatics ligatures of TeX
\setromanfont{Verdana}

\usepackage{paracol} %%Pour les colonnes sur plusieurs pages

\usepackage{multido}

\usepackage{tikz}
\newsavebox{\timepagebox}

\newenvironment*{timepage}{%
  \begin{lrbox}{\timepagebox}%
  \begin{minipage}%
}{%
  \end{minipage}
  \end{lrbox}%
  \noindent
  \begin{tikzpicture}[
    inner sep=0pt,
    outer sep=0pt,
    baseline=0pt,
  ]
  \path (0,0) ++(2em,-\dp\timepagebox)
    node [anchor=south west] {\usebox{\timepagebox}}
  ;
  \draw[
    red,
    line join=round,
    semithick,
  ]
    (.5\pgflinewidth,\ht\timepagebox-.5\pgflinewidth) -- ++(1.6em,0) --
    ++(0,-\ht\timepagebox-\dp\timepagebox+\pgflinewidth+.9em) --
    ++(-.8em,-.8em) -- ++(-.8em,.8em) -- cycle
  ;
  \end{tikzpicture}%
}

\begin{document}

\setlength{\parindent}{0em}
\setlength{\parskip}{0.5em}

\columnratio{0.32}
\begin{paracol}{2}
\begin{leftcolumn}
Left column

\multido{\i=2+1}{30}{bla ble bli\\}

\end{leftcolumn}%
\begin{rightcolumn}%

\textbf{A title for something that is a little bit verbose}

{\scriptsize a comment about it}

\begin{timepage}{0.6\columnwidth}

\begin{itemize}
\item {\footnotesize bla bla bla}
\end{itemize}
{\footnotesize bla bla again}

{\footnotesize bla}

{\footnotesize bla}

\begin{itemize}
\item {\footnotesize bla bla}
\end{itemize}
\end{timepage}
\begin{minipage}{0.28\columnwidth}
{\fbox{Some stuff}}\end{minipage}

\textbf{A second title  that is a little bit verbose}

{\scriptsize a comment about it}

\begin{timepage}{0.6\columnwidth}

\begin{itemize}
\item {bla bla bla}
\end{itemize}
{\footnotesize one thing}

{\footnotesize another one}

{\footnotesize a third one}

{\footnotesize a fourth one}

\begin{itemize}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\item {\footnotesize bla bla}
\end{itemize}
{\footnotesize something else}

{\footnotesize a last thing}
\end{timepage}
\begin{minipage}{0.28\columnwidth}
{\fbox{Some stuff}}
\end{minipage}

\textbf{Another title}

{\scriptsize etc}
\end{rightcolumn}
\end{paracol}
\end{document}